KR102230328B1 - Adhesive composition, adhesive sheet, and optical film - Google Patents

Abstract

It has antistatic properties and suppresses the peeling voltage at the time of peeling of the adherend that is not antistatic, and the adhesive strength at the time of high-speed peeling is small, and at the time of low-speed peeling so that problems such as lifting or peeling do not occur. A pressure-sensitive adhesive composition capable of obtaining a pressure-sensitive adhesive sheet having high adhesive strength and excellent transparency, or an optical film having the pressure-sensitive adhesive sheet attached thereto is provided.
Provides a pressure-sensitive adhesive composition comprising a polymer (A) having a glass transition temperature of less than 0°C and a reactive ionic liquid as monomer units, and containing a polymer (B) having an intrinsic viscosity (dL/g) of 0.01 or more and less than 0.5 do.

Description

A pressure-sensitive adhesive composition, a pressure-sensitive adhesive sheet, and an optical film TECHNICAL FIELD [ADHESIVE COMPOSITION, ADHESIVE SHEET, AND OPTICAL FILM}

The present invention relates to a pressure-sensitive adhesive composition having antistatic properties, a pressure-sensitive adhesive sheet in the form of a sheet or a tape using the same, and an optical film with a pressure-sensitive adhesive sheet.

The pressure-sensitive adhesive sheet formed of the pressure-sensitive adhesive composition having antistatic properties of the present invention is suitably used for plastic products that are susceptible to static electricity. Among them, it is particularly useful as an antistatic adhesive sheet used in applications where static electricity is avoided such as electronic devices, and as a surface protective film used for the purpose of protecting the surface of optical members such as polarizing plates, wavelength plates, optical compensation films, and reflective sheets. Do.

The surface protective film is generally bonded to an object to be protected (an adherend) through an adhesive applied to the side of the protective film, and is used for the purpose of preventing scratches and contamination that occur during processing and transport of the object to be protected. For example, a panel of a liquid crystal display is formed by bonding an optical member such as a polarizing plate or a wave plate to a liquid crystal cell through an adhesive. These optical members bonded to the liquid crystal cell are bonded with a protective film through an adhesive for the purpose of preventing scratches or contamination.

Then, the protective film is peeled off and removed at a stage where the optical member is bonded to the liquid crystal cell, and the protective film becomes unnecessary. In general, since a protective film or an optical member is made of a plastic material, electrical insulation is high, and static electricity is generated during friction or peeling. Therefore, static electricity is generated even when the protective film is peeled from an optical member such as a polarizing plate. If a voltage is applied to the liquid crystal while static electricity remains, the alignment of the liquid crystal molecules is lost or a panel is damaged. Therefore, in order to prevent such a problem, various antistatic treatments are applied to the surface protective film.

For example, a method of preventing charging by adding at least one surfactant to an adhesive and transferring the surfactant from the adhesive to an adherend is disclosed (for example, see Patent Document 1). However, this technique tends to bleed the surface active agent onto the pressure-sensitive adhesive surface, and when applied to a protective film, there is a concern about contamination to the adherend. Therefore, when a pressure-sensitive adhesive to which a low molecular weight surfactant is added is applied to the protective film for optical members, it is difficult to express sufficient antistatic properties without impairing the optical properties of the optical member.

Further, a method of suppressing bleeding of the antistatic agent on the surface of the pressure-sensitive adhesive by adding an antistatic agent composed of a polyether polyol and an alkali metal salt to an acrylic pressure-sensitive adhesive is disclosed (see, for example, Patent Document 2). However, even in this method, bleeding of the antistatic agent is unavoidable, and as a result, when actually applied to a surface protective film, if the treatment under high temperature is performed, contamination to the adherend will occur due to the bleeding phenomenon.

Further, a technique related to an antistatic acrylic pressure-sensitive adhesive containing an acrylic copolymer having an alkylene oxide chain in the side chain and an ionic compound has been disclosed (Patent Document 3), and both antistatic properties and low fouling properties are attained. However, in this method, there is a concern that problems such as lifting and peeling may occur.

Further, there is disclosed a method in which an acrylic copolymer having a quaternary ammonium group in the side chain is added to an acrylic pressure-sensitive adhesive as an antistatic agent to achieve both low fouling properties and antistatic properties (Patent Document 4). However, dimethyl sulfate or diethyl sulfate is used as an alkylating agent that quaternizes the side chain of the acrylic copolymer, and if the alkylating agent remains in the pressure-sensitive adhesive, there is a problem that it may adversely affect the human body. .

As described above, the surface protective film is peeled off when it becomes unnecessary, but is often peeled off at a relatively high speed from the viewpoint of work efficiency. For this reason, when the adhesive force at the time of high-speed peeling is high, work efficiency is inferior, and there exists a problem that the object to be protected, such as an optical member or glass, is damaged at the time of peeling. On the other hand, if the adhesive force at the time of high-speed peeling is to be sufficiently small, problems such as lifting or peeling may occur after punching of the object to be protected or polishing of the end face. In addition, when a surface protection film is used as the surface protection application of an optical member, the inspection step of the adherend is sometimes performed while the surface protection film is bonded, and high transparency is required for the surface protection film itself.

Japanese Patent Application Laid-Open No. Hei 9-165460 Japanese Patent Laid-Open Publication No. Hei6-128539 Japanese Patent Laid-Open No. 2005-206776 Japanese Patent Laid-Open No. 2010-126707

Therefore, in view of such circumstances, the present invention is designed to prevent antistatic and suppress the peeling charge voltage at the time of peeling of an adherend that is not antistatic, and the adhesive force at the time of high-speed peeling is small, and problems such as lifting and peeling. It is an object of the present invention to provide a pressure-sensitive adhesive composition having high adhesion at the time of low-speed peeling and excellent in transparency, and an antistatic pressure-sensitive adhesive sheet using the same, and an optical film with a pressure-sensitive adhesive sheet.

That is, the pressure-sensitive adhesive composition of the present invention contains a polymer (A) having a glass transition temperature of less than 0°C, and a reactive ionic liquid as monomer units, and a polymer (B) having an intrinsic viscosity (dL/g) of 0.01 or more and less than 0.5. Characterized in that.

It is preferable that the pressure-sensitive adhesive composition of the present invention contains 0.05 to 30 parts by mass of the polymer (B) with respect to 100 parts by mass of the polymer (A).

In the pressure-sensitive adhesive composition of the present invention, it is preferable that the polymer (B) is a (meth)acrylic polymer.

In the pressure-sensitive adhesive composition of the present invention, it is preferable that the polymer (B) contains a monomer having a polyoxyalkylene skeleton as a monomer unit.

In the pressure-sensitive adhesive composition of the present invention, it is preferable that the reactive ionic liquid is a reactive ionic liquid represented by the following formulas (1) and/or (2).

[In Formulas 1 and 2, R ¹ is a hydrogen atom or a methyl group, X ⁺ is a cation ^{moiety, and Y-} is an anion. Z represents a C1-C3 alkylene group.]

In the pressure-sensitive adhesive composition of the present invention, it is preferable that the cation moiety is a quaternary ammonium group.

In the pressure-sensitive adhesive composition of the present invention, it is preferable that the anion is a fluorine-containing anion.

In the pressure-sensitive adhesive composition of the present invention, it is preferable that the monomer having the polyoxyalkylene skeleton is an alkylene oxide group-containing reactive monomer having an average added mole number of 3 to 100 oxyalkylene units.

It is preferable that the pressure-sensitive adhesive layer of the present invention is formed of the pressure-sensitive adhesive composition.

It is preferable that the gel fraction of the pressure-sensitive adhesive layer of the present invention is 85.00 to 99.95% by mass.

It is preferable that the pressure-sensitive adhesive sheet of the present invention is formed by forming the pressure-sensitive adhesive layer on at least one side of a base film.

In the pressure-sensitive adhesive sheet of the present invention, it is preferable that the base film is a plastic film.

It is preferable to use the adhesive sheet of this invention for a surface protection application.

It is preferable to use the adhesive sheet of this invention in an electronic component manufacturing/shipping process.

It is preferable that the optical film with an adhesive sheet of this invention attaches the said adhesive sheet to an optical film.

1 is a schematic diagram illustrating the configuration of an adhesive sheet.
2 is a schematic diagram illustrating a peeling electrification voltage test.

Hereinafter, embodiments of the present invention will be described in detail.

In the pressure-sensitive adhesive sheet of the present invention, it is preferable to form the pressure-sensitive adhesive layer on at least one side of the base film. Specifically, as the pressure-sensitive adhesive sheet, a typical configuration example is schematically shown in FIG. 1. Here, the pressure-sensitive adhesive sheet 10 includes a base film 13 (for example, a polyester film) and a pressure-sensitive adhesive layer 12 provided on one side thereof. The pressure-sensitive adhesive sheet 10 is used by attaching the pressure-sensitive adhesive layer 12 to an adherend (to be protected, for example, the surface of an optical component such as a polarizing plate). As shown in Fig. 1, the pressure-sensitive adhesive sheet before use (i.e., before adhesion to an adherend) is a separator in which the surface of the pressure-sensitive adhesive layer (the adhesion surface to the adherend) is at least the side of the pressure-sensitive adhesive layer as a peeling surface ( It may exist in a form protected by 11). Hereinafter, the configuration of the pressure-sensitive adhesive sheet will be described in detail.

The pressure-sensitive adhesive composition of the present invention contains a polymer (A) having a glass transition temperature of less than 0°C and a reactive ionic liquid as monomer units, and contains a polymer (B) if the intrinsic viscosity (dL/g) is 0.01 or more and less than 0.5. It is characterized.

Hereinafter, the polymer (A) and polymer (B) will be described in detail.

[Polymer (A)]

The polymer (A) is not particularly limited as long as the glass transition temperature is less than 0°C, and is generally used as a pressure-sensitive adhesive such as (meth)acrylic polymer, rubber polymer, silicone polymer, polyurethane polymer, polyester polymer, etc. Polymers can be used. In particular, it is suitable to use a (meth)acrylic polymer that is easily compatible with the polymer (B) and has high transparency.

The glass transition temperature (Tg) of the polymer (A) is less than 0°C, preferably less than -10°C, more preferably less than -40°C, and usually more than -80°C. When the glass transition temperature (Tg) of the polymer (A) is 0° C. or higher, the polymer is difficult to flow, the wetting to the adherend is insufficient, and the adhesiveness may decrease.

In the present embodiment, when the polymer (A) is a copolymer (copolymer), the glass transition temperature is a value calculated based on the following equation (Fox equation). On the other hand, it means that the polymer includes a homopolymer (homopolymer) and a copolymer (copolymer composed of a plurality of monomer components).

1/Tg = W ₁ /Tg ₁ +W ₂ /Tg ₂ +···+W _n /Tg _n

[In the formula, Tg is the glass transition temperature (unit: K) of the copolymer, and Tg _i (i=1, 2, ...n) is the glass transition temperature when the monomer i forms a homopolymer (unit: K ), W _i (i=1, 2,...n) represents the mass fraction of all monomer components of the monomer i.]

Further, the glass transition temperature of the monomer i Tg _i is the nominal (公稱) values or the like described literature (e.g., Polymer Handbook, Handbook of pressure-sensitive adhesive, etc.), catalogs.

On the other hand, in the present specification, "the glass transition temperature when homopolymer is formed" means "the glass transition temperature of the homopolymer of the monomer", and only certain monomers (in some cases referred to as "monomer X") It means the glass transition temperature (Tg) of a polymer formed as a monomer component. Specifically, figures are given in the "Polymer Handbook" (3rd edition, John Wiley & Sons, Inc, 1989). On the other hand, the glass transition temperature (Tg) of a homopolymer not described in the literature refers to a value obtained, for example, by the following measuring method. That is, 100 parts by mass of monomer X, 0.2 parts by mass of 2,2'-azobisisobutyronitrile, and 200 parts by mass of ethyl acetate as a polymerization solvent were added to a reactor equipped with a thermometer, agitator, a nitrogen inlet tube, and a reflux cooling tube. And stirred for 1 hour while introducing nitrogen gas. After removing oxygen in the polymerization system in this way, the temperature was raised to 63°C and reacted for 10 hours. Then, it is cooled to room temperature, and a homopolymer solution having a solid content concentration of 33% by mass is obtained. Subsequently, this homopolymer solution is cast onto a release liner and dried to prepare a test sample (sheet-like homopolymer) having a thickness of about 2 mm. Then, about 1 to 2 mg of this test sample was weighed in an open cell made of aluminum, and a temperature-raising rate of 5°C/min under a nitrogen atmosphere of 50 ml/min using a temperature modulated DSC (trade name “Q-2000”, manufactured by TA Instruments). In min, the reversing heat flow (specific heat component) behavior of the homopolymer is obtained. With reference to JIS-K-7121, a straight line equidistant in the vertical axis direction from a straight line extending from the low-temperature side baseline and the high-temperature side baseline of the obtained reversing heat flow, and the curve of the step-like change part of the glass transition The temperature at the point of intersection is taken as the glass transition temperature (Tg) when a homopolymer is used.

Further, the weight average molecular weight (Mw) of the polymer (A) is, for example, preferably 30,000 to 5 million, more preferably 100,000 to 2 million, and still more preferably 200,000 to 1 million. If the weight average molecular weight (Mw) is less than 30,000, the cohesive strength of the pressure-sensitive adhesive is insufficient, and contamination to the adherend is likely to occur in some cases. On the other hand, when the weight average molecular weight (Mw) exceeds 5 million, the fluidity of the pressure-sensitive adhesive is lowered, the wetting to the adherend is insufficient, and the adhesiveness may decrease.

[(Meth)acrylic polymer (a)]

Hereinafter, the (meth)acrylic polymer (a), which is a suitable specific example of the polymer (A), will be described in detail.

The (meth)acrylic polymer (a) is a polymer containing as a monomer unit (component) an alkyl (meth)acrylate having a linear or branched alkyl group having 1 to 20 carbon atoms. In addition, the (meth)acrylic polymer (a) may be composed of an alkyl (meth)acrylate having an alkyl group having 1 to 20 carbon atoms alone or in combination of two or more.

Examples of the (meth)acrylate alkyl ester having an alkyl group having 1 to 20 carbon atoms include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, ( Isobutyl meth)acrylate, s-butyl (meth)acrylate, t-butyl (meth)acrylate, pentyl (meth)acrylate, isopentyl (meth)acrylate, hexyl (meth)acrylate, heptyl (meth)acrylate, (meth) Octyl acrylate, 2-ethylhexyl (meth)acrylate, Isooctyl (meth)acrylate, nonyl (meth)acrylate, isononyl (meth)acrylate, decyl (meth)acrylate, isodecyl (meth)acrylate, (meth) Undecyl acrylic acid, dodecyl (meth)acrylate, tridecyl (meth)acrylate, tetradecyl (meth)acrylate, pentadecyl (meth)acrylate, hexadecyl (meth)acrylate, heptadecyl (meth)acrylate, (meth)acrylic acid octadecyl (meth) acrylate, nonadecyl (meth) acrylate, eicosyl, etc. of (meth) acrylic acid C _{1 -20} alkyl esters [preferably (meth) acrylic acid C _2-14 alkyl ester, more preferably a (meth) there may be mentioned the _10-alkyl ester], such as _acrylic acid C _2. On the other hand, the (meth)acrylate alkyl ester refers to an acrylic acid alkyl ester and/or a methacrylic acid alkyl ester, and "(meth)..." has the same meaning.

The ratio of the (meth)acrylic acid alkyl ester having an alkyl group having 1 to 20 carbon atoms is preferably 50 to 99.9% by mass, more preferably based on the total amount of the monomer unit (component) for preparing the (meth)acrylic polymer (a). It is preferably 60 to 98% by mass, more preferably 70 to 96% by mass. If it is within the above range, it is a preferred aspect because desirable adhesive properties can be obtained for a pressure-sensitive adhesive sheet that can be used for re-peeling.

On the other hand, the (meth)acrylic polymer (a) is for the purpose of modifying cohesive strength, heat resistance, crosslinking properties, etc., and if necessary, other monomer units (components) that can be copolymerized with the (meth)acrylic acid alkyl ester (copolymerizable Monomer) may be included. Accordingly, the (meth)acrylic polymer (a) may contain a copolymerizable monomer together with the (meth)acrylic acid alkyl ester as a main component. As the copolymerizable monomer, a monomer having a polar group can be suitably used. On the other hand, the main component means a monomer having the highest blending ratio among all the monomer components.

As a specific example of the copolymerizable monomer,

Carboxyl group-containing monomers such as acrylic acid, methacrylic acid, carboxyethyl acrylate, carboxypentyl acrylate, itaconic acid, maleic acid, fumaric acid, crotonic acid, and isocrotonic acid;

2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, 8-hydroxyoctyl (meth)acrylate, Hydroxyl group-containing monomers such as hydroxyalkyl (meth)acrylate, such as 10-hydroxydecyl (meth)acrylate, 12-hydroxylauryl (meth)acrylate, and (4-hydroxymethylcyclohexyl)methyl methacrylate ;

Acid anhydride group-containing monomers such as maleic anhydride and itaconic anhydride;

Styrenesulfonic acid, allylsulfonic acid, 2-(meth)acrylamido-2-methylpropanesulfonic acid, (meth)acrylamidopropanesulfonic acid, sulfopropyl (meth)acrylate, (meth)acryloyl Sulfonic acid group-containing monomers such as oxynaphthalenesulfonic acid;

Phosphoric acid group-containing monomers such as 2-hydroxyethylacryloyl phosphate;

(Meth)acrylamide, N,N-dimethyl (meth)acrylamide, N,N-diethyl (meth)acrylamide, N,N-dipropyl (meth)acrylamide, N,N-diisopropyl ( N,N-dialkyl (meth)acrylamides such as meth)acrylamide, N,N-di(n-butyl) (meth)acrylamide, and N,N-di(t-butyl) (meth)acrylamide, N-ethyl (meth)acrylamide, N-isopropyl (meth)acrylamide, N-butyl (meth)acrylamide, Nn-butyl (meth)acrylamide, N-methylol (meth)acrylamide, N-ethyl All (meth)acrylamide, N-methylolpropane (meth)acrylamide, N-methoxymethyl (meth)acrylamide, N-methoxyethyl (meth)acrylamide, N-butoxymethyl (meth)acrylamide (N-substituted) amide-based monomers such as amide and N-acryloylmorpholine;

N-(meth)acryloyloxymethylenesuccinimide, N-(meth)acryloyl-6-oxyhexamethylenesuccinimide, N-(meth)acryloyl-8-oxyhexamethylenesuccinimide, etc. Succinimide-based monomer of;

Maleimide-based monomers such as N-cyclohexylmaleimide, N-isopropylmaleimide, N-laurylmaleimide, and N-phenylmaleimide;

N-methyl itaconimide, N-ethyl itaconimide, N-butyl itaconimide, N-octyl itaconimide, N-2-ethylhexyl itaconimide, N-cyclohexyl itacone Itaconimide-based monomers such as mid and N-lauryl itaconimide;

Vinyl esters such as vinyl acetate and vinyl propionate;

N-vinyl-2-pyrrolidone, N-methylvinylpyrrolidone, N-vinylpyridine, N-vinylpiperidone, N-vinylpyrimidine, N-vinylpiperazine, N-vinylpyrazine, N-vinylpyrrole , N-vinylimidazole, N-vinyloxazole, N-(meth)acryloyl-2-pyrrolidone, N-(meth)acryloylpiperidine, N-(meth)acryloylpyrrolidine , N-vinylmorpholine, N-vinyl-2-piperidone, N-vinyl-3-morpholinone, N-vinyl-2-caprolactam, N-vinyl-1,3-oxazin-2-one, Nitrogen-containing heterocyclic systems such as N-vinyl-3,5-morpholinide, N-vinylpyrazole, N-vinylisoxazole, N-vinylthiazole, N-vinylisothiazole, and N-vinylpyridazine Monomer;

N-vinylcarboxylic acid amides;

Lactam-based monomers such as N-vinyl caprolactam;

Cyanoacrylate monomers such as acrylonitrile and methacrylonitrile;

(Meth)acrylate aminoalkyl such as aminoethyl (meth)acrylate, N,N-dimethylaminoethyl (meth)acrylate, N,N-dimethylaminoethyl (meth)acrylate, and t-butylaminoethyl (meth)acrylate System monomer;

Alkoxyalkyl (meth)acrylate monomers such as methoxyethyl (meth)acrylate, ethoxyethyl (meth)acrylate, propoxyethyl (meth)acrylate, butoxyethyl (meth)acrylate, and ethoxypropyl (meth)acrylate;

Styrene-based monomers such as styrene and α-methylstyrene;

Epoxy group-containing acrylic monomers such as glycidyl (meth)acrylate;

An acrylic acid ester-based monomer having a heterocycle such as tetrahydrofurfuryl (meth)acrylate, a fluorine atom-containing (meth)acrylate, and a silicone (meth)acrylate, a halogen atom, a silicon atom, or the like;

Olefinic monomers such as isoprene, butadiene, and isobutylene;

Vinyl ether-based monomers such as methyl vinyl ether and ethyl vinyl ether;

Vinyl esters such as vinyl acetate and vinyl propionate;

Aromatic vinyl compounds such as vinyl toluene and styrene;

Olefins or dienes such as ethylene, butadiene, isoprene, and isobutylene;

Vinyl ethers such as vinyl alkyl ether;

Vinyl chloride;

Sulfonic acid group-containing monomers such as sodium vinylsulfonate;

Imide group-containing monomers such as cyclohexyl maleimide and isopropyl maleimide;

Isocyanate group-containing monomers such as 2-isocyanatoethyl (meth)acrylate;

Acryloylmorpholine;

(Meth)acrylic acid esters having an alicyclic hydrocarbon group such as cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, and dicyclopentanyl (meth)acrylate;

(Meth)acrylic acid ester having an aromatic hydrocarbon group such as phenyl (meth)acrylate and phenoxyethyl (meth)acrylate;

(Meth)acrylic acid ester obtained from terpene compound derivative alcohol

And the like. On the other hand, these copolymerizable monomers may be used alone or in combination of two or more.

When the (meth)acrylic polymer (a) contains a copolymerizable monomer together with the (meth)acrylic acid alkyl ester as a main component, the hydroxyl group-containing monomer or the carboxyl group-containing monomer can be suitably used. Among them, as the hydroxyl group-containing monomer, 2-hydroxyethyl (meth)acrylate and 4-hydroxybutyl (meth)acrylate are suitable, and acrylic acid can be suitably used as the carboxyl group-containing monomer.

The blending amount of the copolymerizable monomer is not particularly limited, but the copolymerizable monomer is preferably 0.01 to 40% by mass, more preferably based on the total amount of the monomer unit (component) for preparing the (meth)acrylic polymer (a). It is preferably 0.1 to 30% by mass, more preferably 0.5 to 20% by mass. By containing 0.01% by mass or more of the copolymerizable monomer, it is possible to prevent a decrease in the cohesive force of the pressure-sensitive adhesive (adhesive layer, pressure-sensitive adhesive sheet) formed of the pressure-sensitive adhesive composition, and prevent contamination when peeled from the adherend. Further, by setting the blending amount of the copolymerizable monomer to 40% by mass or less, it is possible to prevent excessively high cohesiveness and improve the tack feeling at room temperature (25°C).

Further, the (meth)acrylic polymer (a) may further contain, as a monomer unit (component), an alkylene oxide group-containing reactive monomer having an average added mole number of 3 to 100 oxyalkylene units.

The average number of moles added of the oxyalkylene unit to the alkylene oxide group-containing reactive monomer is preferably 3 to 100, more preferably 4 to 80, and 5 to 50 from the viewpoint of compatibility with the polymer (B). It is particularly preferred. When the average number of added moles is 3 or more, the effect of reducing contamination of the adherend (to be protected) tends to be obtained efficiently. Further, when the average number of added moles is greater than 100, the interaction with the polymer (B) is large, and the pressure-sensitive adhesive composition tends to become a gel, making coating difficult, which is not preferable. On the other hand, the terminal of the oxyalkylene chain in the alkylene oxide group-containing reactive monomer may be a hydroxyl group as it is or may be substituted with another functional group or the like.

The alkylene oxide group-containing reactive monomer may be used alone, or two or more may be used in combination, but the total amount is the total constituent units of the (meth)acrylic polymer (a) (total monomer units ( Ingredients): 100% by mass), preferably 5.0% by mass or less, more preferably 4,0% by mass or less, still more preferably 3.0% by mass or less, and particularly preferably 1.0% by mass or less. If the blending amount of the alkylene oxide group-containing reactive monomer exceeds 5.0% by mass, it is not preferable because it becomes a factor for lowering the adhesive strength.

Examples of the oxyalkylene unit of the alkylene oxide group-containing reactive monomer include those having an alkylene group having 1 to 6 carbon atoms, and examples thereof include an oxymethylene group, an oxyethylene group, an oxypropylene group, and an oxybutylene group. . The hydrocarbon group of the oxyalkylene chain may be linear or branched.

Further, it is more preferable that the alkylene oxide group-containing reactive monomer is a reactive monomer having an ethylene oxide group. By using a (meth)acrylic polymer having a reactive monomer having an ethylene oxide group as the base polymer, the compatibility between the base polymer and the polymer (B) is improved, bleeding to the adherend is suitably suppressed, and a low-pollution pressure-sensitive adhesive composition Is obtained.

Examples of the alkylene oxide group-containing reactive monomer used in the present invention include (meth)acrylic acid alkylene oxide adducts, and reactive surfactants having reactive substituents such as acryloyl group, methacryloyl group, and allyl group in the molecule. Can be mentioned.

As the (meth)acrylic acid alkylene oxide adduct, a compound represented by the following formula (3) can be suitably used.

[In Formula 3, R ₁ is hydrogen or a methyl group, R ₂ is hydrogen or a monovalent organic group, m and p are integers of 2 to 4, n and q are 0 or integers of 2 to 40, and n and q There is no case where is 0 at the same time.]

Specific examples of the (meth)acrylate alkylene oxide adduct include, for example, polyethylene glycol (meth)acrylate, polypropylene glycol (meth)acrylate, polyethylene glycol-polypropylene glycol (meth)acrylate, polyethylene glycol-polybutylene glycol (Meth)acrylate, polypropylene glycol-polybutylene glycol (meth)acrylate, methoxy polyethylene glycol (meth)acrylate, ethoxy polyethylene glycol (meth)acrylate, butoxy polyethylene glycol (meth)acrylate, Octoxy polyethylene glycol (meth)acrylate, lauroxy polyethylene glycol (meth)acrylate, stearoxy polyethylene glycol (meth)acrylate, phenoxy polyethylene glycol (meth)acrylate, methoxy polypropylene glycol (meth)acrylate And octoxy polyethylene glycol-polypropylene glycol (meth)acrylate.

Further, specific examples of the reactive surfactant include, for example, an anionic reactive surfactant having a (meth)acryloyl group or an allyl group, a nonionic reactive surfactant, and a cationic reactive surfactant.

Examples of the anionic reactive surfactant include those represented by the general formulas A1 to A10.

[Formula A1]

[R ₁ in Formula A1 represents hydrogen or a methyl group, R ₂ represents a hydrocarbon group or acyl group having 1 to 30 carbon atoms, X represents an anionic hydrophilic group, R ₃ and R ₄ are the same or different, and have 1 to carbon atoms, The alkylene group of 6 is represented, and the average added mole numbers m and n are 0 to 100, provided that (m+n) represents the number of 3 to 100.]

[Formula A2]

[R ₁ in Formula A2 represents hydrogen or a methyl group, R ₂ and R ₇ are the same or different and represent an alkylene group having 1 to 6 carbon atoms, and R ₃ and R ₅ are the same or different and represent hydrogen or an alkyl group. , R ₄ and R ₆ are the same or different and represent hydrogen, an alkyl group, a benzyl group or a styrene group, X represents an anionic hydrophilic group, and the average number of moles added m and n are 0-100, provided that (m+n) Represents a number from 3 to 100.]

[Formula A3]

[R ₁ in Formula A3 represents hydrogen or a methyl group, R ₂ represents an alkylene group having 1 to 6 carbon atoms, X represents an anionic hydrophilic group, and the average added mole number n represents the number of 3 to 100.]

[Formula A4]

[R ₁ in Formula A4 represents hydrogen or a methyl group, R ₂ represents a hydrocarbon group or acyl group having 1 to 30 carbon atoms, R ₃ and R ₄ are the same or different and represent an alkylene group having 1 to 6 carbon atoms, and X Represents an anionic hydrophilic group, and the average added mole numbers m and n are 0 to 100, provided that (m+n) represents the number of 3 to 100.]

[Formula A5]

[R ₁ in Formula A5 represents a hydrocarbon group, an amino group, or a carboxylic acid residue, R ₂ represents an alkylene group having 1 to 6 carbon atoms, X represents an anionic hydrophilic group, and the average added mole number n represents an integer of 3 to 100. .]

[Formula A6]

[In Formula A6, R ₁ represents a hydrocarbon group having 1 to 30 carbon atoms, R ₂ represents hydrogen or a hydrocarbon group having 1 to 30 carbon atoms, R ₃ represents hydrogen or a propenyl group, and R ₄ represents an alkylene having 1 to 6 carbon atoms. Represents a group, X represents an anionic hydrophilic group, and the average added mole number n represents the number of 3 to 100.]

[Formula A7]

[R ₁ in Formula A7 represents hydrogen or a methyl group, R ₂ and R ₄ are the same or different, represent an alkylene group having 1 to 6 carbon atoms, R ₃ represents a hydrocarbon group having 1 to 30 carbon atoms, and M represents hydrogen, It represents an alkali metal, an ammonium group, or an alkanol ammonium group, and the average number of added moles m and n is 0 to 40, provided that (m+n) represents a number of 3 to 100.]

[Formula A8]

_{[R 1} and R ₅ in Formula A8 are the same or different and represent hydrogen or methyl groups, R ₂ and R ₄ are the same or different, represent an alkylene group having 1 to 6 carbon atoms, and R ₃ represents a C 1 to C 30 Represents a hydrocarbon group, M represents hydrogen, an alkali metal, an ammonium group or an alkanol ammonium group, and the average number of added moles m and n are 0 to 100, provided that (m+n) represents a number of 3 to 100.]

[Formula A9]

[R ₁ in Formula A9 represents an alkylene group having 1 to 6 carbon atoms, R ₂ represents a hydrocarbon group having 1 to 30 carbon atoms, M represents hydrogen, an alkali metal, an ammonium group or an alkanol ammonium group, and the average added mole number n is 3 It represents the number of -100.]

[Formula A10]

[R ₁ , R ₂ and R ₃ in Formula A10 are the same or different and represent hydrogen or methyl group, and R ₄ represents a hydrocarbon group having 0 to 30 carbon atoms (in the case of 0 carbon atoms, it represents no _{R 4 ),} R ₅ and R ₆ are the same or different, represent an alkylene group having 1 to 6 carbon atoms, X represents an anionic hydrophilic group, and the average number of added moles m and n are 0 to 100, provided that (m+n) is 3 to Represents the number of 100.]

X in the above formulas A1 to A6 and A10 represents an anionic hydrophilic group. Examples of the anionic hydrophilic group include those represented by the following formulas a1 to a2.

[Formula a1]

[M ₁ in Formula a1 represents hydrogen, an alkali metal, an ammonium group, or an alkanol ammonium group.]

[Formula a2]

_{[M 2} and M ₃ in Formula a2 are the same or different, and represent hydrogen, an alkali metal, an ammonium group, or an alkanol ammonium group.]

Examples of the nonionic reactive surfactant include those represented by the general formulas N1 to N6.

[Formula N1]

[R ₁ in the formula N1 represents hydrogen or a methyl group, R ₂ represents a hydrocarbon group or acyl group having 1 to 30 carbon atoms, R ₃ and R ₄ are the same or different and represent an alkylene group having 1 to 6 carbon atoms, and the average The number of added moles m and n represents a number of 0 to 100, provided that (m+n) represents a number of 3 to 100.]

[Formula N2]

[R ₁ in the formula N2 represents hydrogen or a methyl group, R ₂ , R ₃ and R ₄ are the same or different, and represent an alkylene group having 1 to 6 carbon atoms, and the average number of added moles n, m and l is 0 to 100. , (n+m+1) represents a number from 3 to 100.]

[Chemical Formula N3]

[R ₁ in the formula N3 represents hydrogen or a methyl group, R ₂ and R ₃ are the same or different and represent an alkylene group having 1 to 6 carbon atoms, and R ₄ represents a hydrocarbon group or an acyl group having 1 to 30 carbon atoms, and the average The number of added moles m and n represents a number of 0 to 100, provided that (m+n) represents a number of 3 to 100.]

[Chemical Formula N4]

_{[R 1} and R ₂ in the formula N4 are the same or different and represent a hydrocarbon group having 1 to 30 carbon atoms, R ₃ represents a hydrogen or propenyl group, R ₄ represents an alkylene group having 1 to 6 carbon atoms, and average addition The number of moles n represents a number from 3 to 100.]

[Formula N5]

_{[R 1} and R ₃ in the formula N5 are the same or different and represent an alkylene group having 1 to 6 carbon atoms, and R ₂ and R ₄ are the same or different and represent hydrogen, a hydrocarbon group having 1 to 30 carbon atoms, or an acyl group. , The average number of added moles m and n are 0 to 100, provided that (m+n) represents the number of 3 to 100.]

[Formula N6]

[R ₁ , R ₂ and R ₃ in the formula N6 are the same or different and represent hydrogen or methyl group, and R ₄ represents a hydrocarbon group having 0 to 30 carbon atoms (in the case of 0 carbon atoms, it represents no _{R 4 ),} R ₅ and R ₆ are the same or different and represent an alkylene group having 1 to 6 carbon atoms, and the average number of added moles m and n are 0 to 100, provided that (m+n) represents the number of 3 to 100.]

In addition, as commercially available products of the alkylene oxide group-containing reactive monomer, for example, Blemmer PME-400, Blemmer PME-1000, Blemmer 50POEP-800B (above, all manufactured by Nippon Oil Corporation), Lattemul PD-420, Lattemul PD -430 (above, all manufactured by Gao Corporation), Adekaliathorpe ER-10, Adekaliathorpe NE-10 (above, all manufactured by Asahi Denka Industrial Co., Ltd.), and the like.

Further, the (meth)acrylic polymer (a) may contain a polyfunctional monomer as necessary in order to adjust the cohesive force of the pressure-sensitive adhesive (layer) to be formed.

Examples of the polyfunctional monomer include (poly) ethylene glycol di (meth) acrylate, (poly) propylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, pentaerythritol di (meth) acrylate. , Pentaerythritol tri(meth)acrylate, dipentaerythritol hexa(meth)acrylate, 1,2-ethylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,12-dodecanediol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, tetramethylolmethane tri(meth)acrylate, allyl(meth)acrylate, vinyl (meth) Acrylate, divinylbenzene, epoxy acrylate, polyester acrylate, urethane acrylate, butyl di(meth)acrylate, hexyl di(meth)acrylate, and the like. Among them, trimethylolpropane tri(meth)acrylate, hexanediol di(meth)acrylate, and dipentaerythritol hexa(meth)acrylate can be suitably used. Polyfunctional (meth)acrylates may be used alone or in combination of two or more.

The blending amount of the polyfunctional monomer varies depending on its molecular weight, the number of functional groups, etc., but is 0.01 to 3.0% by mass, preferably 0.02 to 2.0% by mass, based on the total amount of the monomer unit (component) for preparing the (meth)acrylic polymer (a). %, more preferably 0.03 to 1.0 mass%. When the blending amount of the multifunctional monomer exceeds 3.0% by mass with respect to the total amount of the monomer unit (component) for preparing the (meth)acrylic polymer (a), for example, the cohesive force of the pressure-sensitive adhesive (layer) becomes too high, and the adhesive strength (high-speed peeling Force, low-speed peeling force) may decrease. On the other hand, if it is less than 0.01% by mass, for example, the cohesive force of the pressure-sensitive adhesive (layer) decreases, and when peeled from the adherend (to be protected), contamination may occur.

Further, in order to adjust the molecular weight of the (meth)acrylic polymer (a), a chain transfer agent can be used during the polymerization. Examples of the chain transfer agent to be used include compounds having a mercapto group such as octyl mercaptan, lauryl mercaptan, t-dodecyl mercaptan, mercaptoethanol, and α-thioglycerol; Thioglycolic acid, methyl thioglycolate, ethyl thioglycolate, propyl thioglycolic acid, butyl thioglycolic acid, t-butyl thioglycolic acid, 2-ethylhexyl thioglycolic acid, thioglycolic acid Thioglycolic acid esters such as octyl, decyl thioglycolate, dodecyl thioglycolic acid, thioglycolic acid ester of ethylene glycol, thioglycolic acid ester of neopentyl glycol, and thioglycolic acid ester of pentaerythritol Ryu; α-methylstyrene dimers and the like.

In the preparation of the (meth)acrylic polymer (a), a (meth)acrylic polymer is easily formed by using a curing reaction by heat or ultraviolet rays using a polymerization initiator such as a thermal polymerization initiator or a photopolymerization initiator (photoinitiator). can do. In particular, thermal polymerization can be suitably used because of the advantage of shortening the polymerization time. The polymerization initiator may be used alone or in combination of two or more.

As the thermal polymerization initiator, for example, an azo polymerization initiator (e.g., 2,2'-azobisisobutyronitrile, 2,2'-azobis-2-methylbutyronitrile, 2,2'-azobis (2-Methylpropionic acid)dimethyl, 4,4'-azobis-4-cyanovaleric acid, azobisisovaleronitrile, 2,2'-azobis(2-amidinopropane)dihydrochloride , 2,2'-azobis[2-(5-methyl-2-imidazolin-2-yl)propane]dihydrochloride, 2,2'-azobis(2-methylpropionamidine) disulfate , 2,2'-azobis(N,N'-dimethyleneisobutylamidine)dihydrochloride, etc.); Peroxide polymerization initiators (eg, dibenzoyl peroxide, t-butyl permaleate, lauroyl peroxide, etc.); Redox polymerization initiators, etc. are mentioned.

The blending amount of the thermal polymerization initiator is not particularly limited, but, for example, 0.01 to 5 parts by mass is preferable based on 100 parts by mass of the total amount of the monomer unit (component) for preparing the (meth)acrylic polymer (a), and more preferably It is blended in an amount within the range of 0.05 to 3 parts by mass.

The photoinitiator is not particularly limited, but for example, a benzoin ether photoinitiator, an acetophenone photoinitiator, an α-ketol photoinitiator, an aromatic sulfonyl chloride photoinitiator, a photoactive oxime photoinitiator, a benzoin photoinitiator, Benzyl photoinitiators, benzophenone photoinitiators, ketal photoinitiators, thioxanthone photoinitiators, acylphosphine oxide photoinitiators, and the like can be used.

Specifically, examples of the benzoin ether photoinitiator include benzoin methyl ether, benzoin ethyl ether, benzoin propyl ether, benzoin isopropyl ether, benzoin isobutyl ether, 2,2- Dimethoxy-1,2-diphenylethan-1-one [brand name: Igacure 651, the BASF company make], anisole methyl ether, etc. are mentioned. Examples of acetophenone-based photoinitiators include 1-hydroxycyclohexylphenyl ketone [trade name: Igacure 184, manufactured by BASF], 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, 1-[ 4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one [brand name: Igacure 2959, manufactured by BASF Corporation], 2-hydroxy-2-methyl- 1-phenyl-propan-1-one [brand name: Darocure 1173, the BASF company make], methoxyacetophenone, etc. are mentioned. Examples of the α-ketol photopolymerization initiator include 2-methyl-2-hydroxypropiophenone, 1-[4-(2-hydroxyethyl)-phenyl]-2-hydroxy-2-methylpropan-1-one And the like. As an aromatic sulfonyl chloride type photoinitiator, 2-naphthalene sulfonyl chloride etc. are mentioned, for example. As a photoactive oxime type photoinitiator, 1-phenyl-1,1-propanedione-2-(o-ethoxycarbonyl)-oxime, etc. are mentioned, for example.

Moreover, benzoin etc. are contained in the said benzoin-type photoinitiator, for example. Examples of the benzyl photopolymerization initiator include benzyl and the like. Examples of the benzophenone-based photoinitiators include benzophenone, benzoylbenzoic acid, 3,3'-dimethyl-4-methoxybenzophenone, polyvinylbenzophenone, α-hydroxycyclohexylphenylketone, and the like. The ketal photopolymerization initiator includes, for example, benzyl dimethyl ketal and the like. Thioxanthone photoinitiators include, for example, thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2,4-dimethylthioxanthone, isopropylthioxanthone, 2,4-dichlorothio Xanthone, 2,4-diethyl thioxanthone, isopropyl thioxanthone, 2,4-diisopropyl thioxanthone, dodecyl thioxanthone, and the like are included.

Examples of the acylphosphine-based photopolymerization initiator include bis(2,6-dimethoxybenzoyl)phenylphosphine oxide, bis(2,6-dimethoxybenzoyl)(2,4,4-trimethylpentyl)phosphine oxide. , Bis(2,6-dimethoxybenzoyl)-n-butylphosphine oxide, bis(2,6-dimethoxybenzoyl)-(2-methylpropan-1-yl)phosphine oxide, bis(2, 6-dimethoxybenzoyl)-(1-methylpropan-1-yl)phosphine oxide, bis(2,6-dimethoxybenzoyl)-t-butylphosphine oxide, bis(2,6-dimethoxy Benzoyl)cyclohexylphosphine oxide, bis(2,6-dimethoxybenzoyl)octylphosphine oxide, bis(2-methoxybenzoyl)(2-methylpropan-1-yl)phosphine oxide, bis(2- Methoxybenzoyl)(1-methylpropan-1-yl)phosphine oxide, bis(2,6-diethoxybenzoyl)(2-methylpropan-1-yl)phosphine oxide, bis(2,6-di Ethoxybenzoyl)(1-methylpropan-1-yl)phosphine oxide, bis(2,6-dibutoxybenzoyl)(2-methylpropan-1-yl)phosphine oxide, bis(2,4-di Methoxybenzoyl)(2-methylpropan-1-yl)phosphine oxide, bis(2,4,6-trimethylbenzoyl)(2,4-dipentoxyphenyl)phosphine oxide, bis(2,6- Dimethoxybenzoyl)benzylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2-phenylpropylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2-phenylethylphosphine oxide, Bis(2,6-dimethoxybenzoyl)benzylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2-phenylpropylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2- Phenylethylphosphine oxide, 2,6-dimethoxybenzoylbenzylbutylphosphine oxide, 2,6-dimethoxybenzoylbenzyloctylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-2,5 -Diisopropylphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-2-methylphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-4-methylphenylphosphine oxide, bis (2,4,6-trimethylbenzoyl)-2,5-diethylphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-2,3,5,6-tetramethylphenylphosphine oxide, Bis(2,4,6-trimethylbenzoyl)-2,4-di- n-butoxyphenylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide, bis (2,4,6-trimethylbenzoyl)isobutylphosphine oxide, 2,6-dimethoxybenzoyl-2,4,6-trimethylbenzoyl-n-butylphosphine oxide, bis(2,4,6 -Trimethylbenzoyl)phenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-2,4-dibutoxyphenylphosphine oxide, 1,10-bis[bis(2,4,6-tri Methylbenzoyl)phosphine oxide]decane, tri(2-methylbenzoyl)phosphine oxide, and the like.

The blending amount of the photopolymerization initiator is not particularly limited, for example, 0.01 to 5 parts by mass, more preferably 0.05 to 3 parts by mass, based on 100 parts by mass of the total amount of the monomer component to prepare the (meth)acrylic polymer (a). It is formulated in an amount within the range. Here, when the blending amount of the photopolymerization initiator is less than 0.01 parts by mass, the polymerization reaction may become insufficient. When the blending amount of the photopolymerization initiator exceeds 5 parts by mass, the photopolymerization initiator absorbs the ultraviolet rays, so that the ultraviolet rays do not reach the inside of the pressure-sensitive adhesive layer in some cases. In this case, a decrease in the polymerization rate occurs or the molecular weight of the resulting polymer decreases. And by this, the cohesive force of the adhesive (layer) to be formed is lowered, and when the adhesive layer is peeled from the film, a part of the adhesive layer remains in the film, and the film cannot be reused in some cases.

In the present invention, the (meth)acrylic polymer (a) is a partial polymer ((meth)acrylic polymer syrup in which the monomer component is partially polymerized by irradiating ultraviolet (UV) light to a mixture of the monomer component and the polymerization initiator. ) Can also be prepared. The (meth)acrylic polymer syrup is mixed with a polymer (B) to be described later to prepare a pressure-sensitive adhesive composition, and the pressure-sensitive adhesive composition is applied to a predetermined target object (substrate film, etc.), followed by irradiation with ultraviolet rays to complete polymerization. have.

The method of obtaining the polymer (A) (especially (meth)acrylic polymer (a)) is not particularly limited, and polymers (A) such as solution polymerization, emulsion polymerization, bulk polymerization, suspension polymerization, and radiation curing polymerization (especially (meth)acrylic polymer (a)) are not particularly limited. ) As a synthesis method of the acrylic polymer (a)), the polymer can be obtained by applying various polymerization methods generally used. When using the pressure-sensitive adhesive sheet of the present invention as a surface protection sheet described later, solution polymerization and emulsion polymerization can be suitably used from the viewpoint of productivity of the pressure-sensitive adhesive sheet. In addition, any polymer, such as a random copolymer, a block copolymer, an alternating copolymer, and a graft copolymer, may be sufficient as the polymer obtained.

[Polymer (B)]

Polymer (B) is a polymer characterized in that it contains a reactive ionic liquid as a monomer unit and has an intrinsic viscosity (dL/g) of 0.01 or more and less than 0.5, and functions as an antistatic component in the pressure-sensitive adhesive composition of the present invention. Although it does not specifically limit as long as it is a polymer containing a reactive ionic liquid as a monomer unit, (meth)acrylic polymer with high transparency is suitable.

The intrinsic viscosity (dL/g) of the polymer (B) is 0.01 or more and less than 0.5, preferably 0.015 or more and less than 0.49, and more preferably 0.02 or more and less than 0.48. When the intrinsic viscosity of the polymer (B) is within the above range, appropriate compatibility with the polymer (A) is expressed, an adhesive composition (adhesive layer, adhesive sheet) having high transparency is obtained, and a preferred embodiment is obtained. In addition, the pressure-sensitive adhesive (adhesive layer, pressure-sensitive adhesive sheet) formed by using the pressure-sensitive adhesive composition containing the polymer (B) having a specific range of intrinsic viscosity has a low adhesive strength during high-speed peeling, and problems such as lifting or peeling The adhesive strength at the time of low-speed peeling can be sufficiently increased to the extent that there is no occurrence. For that reason, the polymer (B) containing a reactive ionic liquid having an intrinsic viscosity within a certain range as a monomer unit is appropriately compatible with the polymer (A) and is unevenly distributed on the surface of the pressure-sensitive adhesive, thereby expressing antistatic properties, and at the time of high-speed peeling. It is presumed that this is because the increase in adhesive force of is suppressed. Incidentally, the intrinsic viscosity is a value measured based on a method in accordance with JIS-K7367-1.

The polymer (B) of the present invention contains a reactive ionic liquid as an essential component as a monomer unit (component). On the other hand, the "reactive ionic liquid" in the present invention is an ionic liquid having a functional group having a polymerizable (reactive double bond) in the cation moiety and/or anion moiety (either or both) constituting the ionic liquid, It is a liquid (liquid) at any temperature within the range of 0 to 150°C, and is a nonvolatile molten salt, which means that it has transparency. On the other hand, examples of the polymerizable functional group include a vinyl group, an allyl group, and a (meth)acryloyl group. Among them, from the viewpoint of copolymerization, a (meth)acryloyl group and a vinyl group are preferable, and a (meth)acryloyl group is particularly preferable.

The cation moiety of the reactive ionic liquid can be used without particular limitation, but quaternary ammonium cation, imidazolium cation, pyridinium cation, piperidinium cation, pyrrolidinium cation, quaternary phosphonium cation, trialkyl Sulfonium cation, pyrrole cation, pyrazolium cation, and guanidium cation, among others, quaternary ammonium cation, imidazolium cation, pyridinium cation, piperidinium cation, pyrrolidinium cation, and agent. It is more preferable to use a quaternary phosphonium cation or a trialkylsulfonium cation.

Further, as the anion of the anion portion constituting the reactive ionic _{^{liquid, SCN -, BF 4 -,}} PF 6 -, NO 3 -, CH 3 COO -, CF 3 COO -, CH 3 SO 3 -, CF 3 SO _{^{3 -, (FSO 2) 2}} N -, (CF 3 SO 2) 2 N -, (CF 3 SO 2) 3 C -, AsF 6 -, SbF 6 -, NbF 6 -, TaF 6 -, F (HF _{^{) n -, (CN) 2}} N -, C 4 F 9 SO 3 -, (C 2 F 5 SO 2) 2 N -, C 3 F 7 COO -, (CF 3 SO 2) (CF 3 CO) N _{^{-, B (CN) 4 -}} , C (CN) 3 -, N (CN) 2 -, CH 3 OSO 3 -, C 2 H 5 OSO 3 -, C 4 H 9 OSO 3 -, C 6 H 13 OSO _{^{3 -, C 8 H 17 OSO}} 3 -, p- toluenesulfonate anion, a 2- (2-methoxyethyl) ethyl sulfate _{anion, (C 2 F 5) 3} PF 3 - , and the like, in particular a fluorine atom The anion component (fluorine-containing anion) containing an ionic liquid having a low melting point can be obtained, and is preferable because it is excellent in antistatic properties. On the other hand, as an anion, it is preferable not to use a chlorine ion, a bromine ion, etc. from the point of having corrosiveness.

As the reactive ionic liquid, it is appropriately selected and used from a combination of the cation moiety and an anion moiety, and specifically, various ionic liquids shown below are exemplified.

As an imidazolium cationic ionic liquid,

1-alkyl-3-vinylimidazolium tetrafluoroborate, 1-alkyl-3-vinylimidazolium trifluoroacetate, 1-alkyl-3-vinylimidazolium heptafluorobutyrate, 1-alkyl- 3-vinylimidazolium trifluoromethanesulfonate, 1-alkyl-3-vinylimidazolium perfluorobutanesulfonate, 1-alkyl-3-vinylimidazolium bis(trifluoromethanesulfonyl )Imide, 1-alkyl-3-vinylimidazolium bis(pentafluoroethanesulfonyl)imide, 1-alkyl-3-vinylimidazolium tris(trifluoromethanesulfonyl)imide, 1- Alkyl-3-vinylimidazolium hexafluorophosphate, 1-alkyl-3-vinylimidazolium (trifluoromethanesulfonyl) trifluoroacetamide, 1-alkyl-3-vinylimidazolium dicyanide Ionic liquids containing 1-alkyl-3-vinylimidazolium cations such as amide and 1-alkyl-3-vinylimidazolium thiocyanate,

1,2-dialkyl-3-vinylimidazolium bis(fluorosulfonyl)imide, 1,2-dialkyl-3-vinylimidazolium bis(trifluoromethanesulfonyl)imide, 1, 1,2-dialkyl-3-vinylimidazolium cations such as 2-dialkyl-3-vinylimidazolium dicyanamide and 1,2-dialkyl-3-vinylimidazolium thiocyanate Containing ionic liquid,

2-alkyl-1,3-divinylimidazolium bis(fluorosulfonyl)imide, 2-alkyl-1,3-divinylimidazolium bis(trifluoromethanesulfonyl)imide, 2- 2-alkyl-1,3-divinylimidazolium cations such as alkyl-1,3-divinylimidazolium dicyanamide and 2-alkyl-1,3-divinylimidazolium thiocyanate Containing ionic liquid,

1-vinylimidazolium bis(fluorosulfonyl)imide, 1-vinylimidazolium bis(trifluoromethanesulfonyl)imide, 1-vinylimidazolium disyanamide, 1-vinylimida 1-vinyl imidazolium cation-containing ionic liquids such as zolium thiocyanate,

1-alkyl-3-(meth)acryloyloxyalkylimidazolium tetrafluoroborate, 1-alkyl-3-(meth)acryloyloxyalkylimidazolium trifluoroacetate, 1-alkyl-3- (Meth)acryloyloxyalkylimidazolium heptafluorobutyrate, 1-alkyl-3-(meth)acryloyloxyalkylimidazolium trifluoromethanesulfonate, 1-alkyl-3-(meth) )Acryloyloxyalkylimidazolium perfluorobutanesulfonate, 1-alkyl-3-(meth)acryloyloxyalkylimidazolium bis(trifluoromethanesulfonyl)imide, 1-alkyl- 3-(meth)acryloyloxyalkylimidazolium bis(pentafluoroethanesulfonyl)imide, 1-alkyl-3-(meth)acryloyloxyalkylimidazolium tris(trifluoromethanesulfonyl) )Imide, 1-alkyl-3-(meth)acryloyloxyalkylimidazolium hexafluorophosphate, 1-alkyl-3-(meth)acryloyloxyalkylimidazolium (trifluoromethanesulfonyl ) Trifluoroacetamide, 1-alkyl-3-(meth)acryloyloxyalkylimidazolium dicyanamide, 1-alkyl-3-(meth)acryloyloxyalkylimidazolium thiocya 1-alkyl-3-(meth)acryloyloxyalkylimidazolium cation-containing ionic liquids such as nate,

1-alkyl-3-(meth)acryloylaminoalkylimidazolium tetrafluoroborate, 1-alkyl-3-(meth)acryloylaminoalkylimidazolium trifluoroacetate, 1-alkyl-3- (Meth)acryloylaminoalkylimidazolium heptafluorobutyrate, 1-alkyl-3-(meth)acryloylaminoalkylimidazolium trifluoromethanesulfonate, 1-alkyl-3-(meth) )Acryloylaminoalkylimidazolium perfluorobutanesulfonate, 1-alkyl-3-(meth)acryloylaminoalkylimidazolium bis(trifluoromethanesulfonyl)imide, 1-alkyl- 3-(meth)acryloylaminoalkylimidazolium bis(pentafluoroethanesulfonyl)imide, 1-alkyl-3-(meth)acryloylaminoalkylimidazolium tris(trifluoromethanesulfonyl) )Imide, 1-alkyl-3-(meth)acryloylaminoalkylimidazolium hexafluorophosphate, 1-alkyl-3-(meth)acryloylaminoalkylimidazolium (trifluoromethanesulfonyl ) Trifluoroacetamide, 1-alkyl-3-(meth)acryloylaminoalkylimidazolium dicyanamide, 1-alkyl-3-(meth)acryloylaminoalkylimidazolium thiosia 1-alkyl-3-(meth)acryloylaminoalkylimidazolium cation-containing ionic liquids such as nate,

1,2-dialkyl-3-(meth)acryloyloxyalkylimidazolium bis(fluorosulfonyl)imide, 1,2-dialkyl-3-(meth)acryloyloxyalkylimidazolium Bis(trifluoromethanesulfonyl)imide, 1,2-dialkyl-3-(meth)acryloyloxyalkylimidazolium dicyanamide, 1,2-dialkyl-3-(meth)acrylic 1,2-dialkyl-3-(meth)acryloyloxyalkylimidazolium cation-containing ionic liquids such as royloxyalkylimidazolium thiocyanate,

1,2-dialkyl-3-(meth)acryloylaminoalkylimidazolium bis(fluorosulfonyl)imide, 1,2-dialkyl-3-(meth)acryloylaminoalkylimidazolium Bis(trifluoromethanesulfonyl)imide, 1,2-dialkyl-3-(meth)acryloylaminoalkylimidazolium dicyanamide, 1,2-dialkyl-3-(meth)acrylic 1,2-dialkyl-3-(meth)acryloylaminoalkylimidazolium cation-containing ionic liquids such as roylaminoalkylimidazolium thiocyanate,

2-alkyl-1,3-di(meth)acryloyloxyalkylimidazolium bis(fluorosulfonyl)imide, 2-alkyl-1,3-di(meth)acryloyloxyalkylimidazolium Bis(trifluoromethanesulfonyl)imide, 2-alkyl-1,3-di(meth)acryloyloxyalkylimidazolium dicyanamide, 2-alkyl-1,3-di(meth)acrylic 2-alkyl-1,3-di(meth)acryloyloxyalkylimidazolium cation-containing ionic liquids such as royloxyimidazolium thiocyanate,

2-alkyl-1,3-di(meth)acryloylaminoalkylimidazolium bis(fluorosulfonyl)imide, 2-alkyl-1,3-di(meth)acryloylaminoalkylimidazolium Bis(trifluoromethanesulfonyl)imide, 2-alkyl-1,3-di(meth)acryloylaminoalkylimidazolium dicyanamide, 2-alkyl-1,3-di(meth)acrylic 2-alkyl-1,3-di(meth)acryloyloxyalkylimidazolium cation-containing ionic liquids such as roylaminoimidazolium thiocyanate,

1-(meth)acryloyloxyalkylimidazolium bis(fluorosulfonyl)imide, 1-(meth)acryloyloxyalkylimidazolium bis(trifluoromethanesulfonyl)imide, 1- 1-(meth)acryloyloxyalkylimidazolium cations such as (meth)acryloyloxyalkylimidazolium dicyanamide and 1-(meth)acryloyloxyalkylimidazolium thiocyanate Containing ionic liquid,

1-(meth)acryloylaminoalkylimidazolium bis(fluorosulfonyl)imide, 1-(meth)acryloylaminoalkylimidazolium bis(trifluoromethanesulfonyl)imide, 1- 1-(meth)acryloylaminoalkylimidazolium cations such as (meth)acryloylaminoalkylimidazolium dicyanamide and 1-(meth)acryloylaminoalkylimidazolium thiocyanate Containing ionic liquids.

On the other hand, the alkyl substituent is preferably an alkyl group having 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, and more preferably 1 to 6 carbon atoms.

As a pyridinium cationic ionic liquid,

1-vinylpyridinium bis(fluorosulfonyl)imide, 1-vinylpyridinium bis(trifluoromethanesulfonyl)imide, 1-vinylpyridinium dicyanamide, 1-vinylpyridinium thiocylate 1-vinylpyridinium cation-containing ionic liquids such as anate,

1-(meth)acryloyloxyalkylpyridinium bis(fluorosulfonyl)imide, 1-(meth)acryloyloxyalkylpyridinium bis(trifluoromethanesulfonyl)imide, 1-(meth ) Ionic liquids containing 1-(meth)acryloyloxyalkylpyridinium cations such as acryloyloxyalkylpyridinium dicyanamide and 1-(meth)acryloyloxyalkylpyridinium thiocyanate,

1-(meth)acryloylaminoalkylpyridinium bis(fluorosulfonyl)imide, 1-(meth)acryloylaminoalkylpyridinium bis(trifluoromethanesulfonyl)imide, 1-(meth) ) Ionic liquids containing 1-(meth)acryloylaminoalkylpyridinium cations such as acryloylaminoalkylpyridinium dicyanamide and 1-(meth)acryloylaminoalkylpyridinium thiocyanate,

2-alkyl-1-vinylpyridinium bis(fluorosulfonyl)imide, 2-alkyl-1-vinylpyridinium bis(trifluoromethanesulfonyl)imide, 2-alkyl-1-vinylpyridinium Ionic liquids containing 2-alkyl-1-vinylpyridinium cations such as isianamide and 2-alkyl-1-vinylpyridinium thiocyanate,

2-alkyl-1-(meth)acryloyloxyalkylpyridinium bis(fluorosulfonyl)imide, 2-alkyl-1-(meth)acryloyloxyalkylpyridinium bis(trifluoromethanesulfonyl) ) Imide, 2-alkyl-1-(meth)acryloyloxyalkylpyridinium dicyanamide, 2-alkyl-1-(meth)acryloyloxyalkylpyridinium thiocyanate, etc. An ionic liquid containing an alkyl-1-(meth)acryloyloxyalkylpyridinium cation,

2-alkyl-1-(meth)acryloylaminoalkylpyridinium bis(fluorosulfonyl)imide, 2-alkyl-1-(meth)acryloylaminoalkylpyridinium bis(trifluoromethanesulfonyl) ) Imide, 2-alkyl-1-(meth)acryloylaminoalkylpyridinium dicyanamide, 2-alkyl-1-(meth)acryloylaminoalkylpyridinium thiocyanate, etc. An ionic liquid containing an alkyl-1-(meth)acryloylaminoalkylpyridinium cation,

3-alkyl-1-vinylpyridinium bis(fluorosulfonyl)imide, 3-alkyl-1-vinylpyridinium bis(trifluoromethanesulfonyl)imide, 3-alkyl-1-vinylpyridinium Ionic liquid containing 3-alkyl-1-vinylpyridinium cations such as isianamide and 3-alkyl-1-vinylpyridinium thiocyanate,

3-alkyl-1-(meth)acryloyloxyalkylpyridinium bis(fluorosulfonyl)imide, 3-alkyl-1-(meth)acryloyloxyalkylpyridinium bis(trifluoromethanesulfonyl) ) Imide, 3-alkyl-1-(meth)acryloyloxyalkylpyridinium dicyanamide, 3-alkyl-1-(meth)acryloyloxyalkylpyridinium thiocyanate, etc. An ionic liquid containing an alkyl-1-(meth)acryloyloxyalkylpyridinium cation,

3-alkyl-1-(meth)acryloylaminoalkylpyridinium bis(fluorosulfonyl)imide, 3-alkyl-1-(meth)acryloylaminoalkylpyridinium bis(trifluoromethanesulfonyl) ) Imide, 3-alkyl-1-(meth)acryloylaminoalkylpyridinium dicyanamide, 3-alkyl-1-(meth)acryloylaminoalkylpyridinium thiocyanate, etc. An ionic liquid containing an alkyl-1-(meth)acryloylaminoalkylpyridinium cation,

4-alkyl-1-vinylpyridinium bis(fluorosulfonyl)imide, 4-alkyl-1-vinylpyridinium bis(trifluoromethanesulfonyl)imide, 4-alkyl-1-vinylpyridinium Ionic liquids containing 4-alkyl-1-vinylpyridinium cations such as isianamide and 4-alkyl-1-vinylpyridinium thiocyanate,

4-alkyl-1-(meth)acryloyloxyalkylpyridinium bis(fluorosulfonyl)imide, 4-alkyl-1-(meth)acryloyloxyalkylpyridinium bis(trifluoromethanesulfonyl) ) Imide, 4-alkyl-1-(meth)acryloyloxyalkylpyridinium dicyanamide, 4-alkyl-1-(meth)acryloyloxyalkylpyridinium thiocyanate, etc. An ionic liquid containing an alkyl-1-(meth)acryloyloxyalkylpyridinium cation,

4-alkyl-1-(meth)acryloylaminoalkylpyridinium bis(fluorosulfonyl)imide, 4-alkyl-1-(meth)acryloylaminoalkylpyridinium bis(trifluoromethanesulfonyl) ) Imide, 4-alkyl-1-(meth)acryloylaminoalkylpyridinium dicyanamide, 4-alkyl-1-(meth)acryloylaminoalkylpyridinium thiocyanate, etc. And an ionic liquid containing an alkyl-1-(meth)acryloylaminoalkylpyridinium cation.

On the other hand, the alkyl substituent is preferably an alkyl group having 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, and more preferably 1 to 6 carbon atoms.

As a piperidinium cationic ionic liquid,

1-alkyl-1-vinylalkylpiperidinium bis(fluorosulfonyl)imide, 1-alkyl-1-vinylalkylpiperidinium bis(trifluoromethanesulfonyl)imide, 1-alkyl-1- 1-alkyl-1-vinylalkylpiperidinium cation-containing ionic liquids such as vinylalkylpiperidinium dicyanamide and 1-alkyl-1-vinylalkylpiperidinium thiocyanate,

1-alkyl-1-(meth)acryloyloxyalkylpiperidinium bis(fluorosulfonyl)imide, 1-alkyl-1-(meth)acryloyloxyalkylpiperidinium bis(trifluoromethe) Insulfonyl)imide, 1-alkyl-1-(meth)acryloyloxyalkylpiperidinium dicyanamide, 1-alkyl-1-(meth)acryloyloxyalkylpiperidinium thiocyanate 1-alkyl-1-(meth)acryloyloxyalkylpiperidinium cation-containing ionic liquids such as,

1-alkyl-1-(meth)acryloylaminoalkylpiperidinium bis(fluorosulfonyl)imide, 1-alkyl-1-(meth)acryloylaminoalkylpiperidinium bis(trifluoromethe) Insulfonyl)imide, 1-alkyl-1-(meth)acryloylaminoalkylpiperidinium dicyanamide, 1-alkyl-1-(meth)acryloylaminoalkylpiperidinium thiocyanate 1-alkyl-1-(meth)acryloylaminoalkylpiperidinium cation-containing ionic liquids such as are mentioned.

On the other hand, the alkyl substituent is preferably an alkyl group having 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, and more preferably 1 to 6 carbon atoms.

As a pyrrolidinium cationic liquid,

1-alkyl-1-vinylalkylpyrrolidinium bis(fluorosulfonyl)imide, 1-alkyl-1-vinylalkylpyrrolidinium bis(trifluoromethanesulfonyl)imide, 1-alkyl-1- 1-alkyl-1-vinylalkylpyrrolidinium cation-containing ionic liquids such as vinylalkylpyrrolidinium dicyanamide and 1-alkyl-1-vinylalkylpyrrolidinium thiocyanate,

1-alkyl-1-(meth)acryloyloxyalkylpyrrolidinium bis(fluorosulfonyl)imide, 1-alkyl-1-(meth)acryloyloxyalkylpyrrolidinium bis(trifluoromethe) Insulfonyl)imide, 1-alkyl-1-(meth)acryloyloxyalkylpyrrolidinium dicyanamide, 1-alkyl-1-(meth)acryloyloxyalkylpyrrolidinium thiocyanate 1-alkyl-1-(meth)acryloyloxyalkylpyrrolidinium cation-containing ionic liquids such as,

1-alkyl-1-(meth)acryloylaminoalkylpyrrolidinium bis(fluorosulfonyl)imide, 1-alkyl-1-(meth)acryloylaminoalkylpyrrolidinium bis(trifluoromethe) Insulfonyl)imide, 1-alkyl-1-(meth)acryloylaminoalkylpyrrolidinium dicyanamide, 1-alkyl-1-(meth)acryloylaminoalkylpyrrolidinium thiocyanate And 1-alkyl-1-(meth)acryloylaminoalkylpyrrolidinium cation-containing ionic liquids.

On the other hand, the alkyl substituent is preferably an alkyl group having 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, and more preferably 1 to 6 carbon atoms.

As a trialkylsulfonium cationic ionic liquid,

Dialkyl(vinyl)sulfonium bis(fluorosulfonyl)imide, dialkyl(vinyl)sulfonium bis(trifluoromethanesulfonyl)imide, dialkyl(vinyl)sulfonium dicyanamide, dialkyl Dialkyl (vinyl) sulfonium cation-containing ionic liquids such as (vinyl) sulfonium thiocyanate, etc.,

Dialkyl((meth)acryloyloxyalkyl)sulfonium bis(fluorosulfonyl)imide, dialkyl((meth)acryloyloxyalkyl)sulfonium bis(trifluoromethanesulfonyl)imide, Dialkyl ((meth)acryloyloxy, such as dialkyl((meth)acryloyloxyalkyl)sulfonium dicyanamide, dialkyl((meth)acryloyloxyalkyl)sulfonium thiocyanate, etc. Alkyl) sulfonium cation-containing ionic liquid,

Dialkyl((meth)acryloylaminoalkyl)sulfonium bis(fluorosulfonyl)imide, dialkyl((meth)acryloylaminoalkyl)sulfonium bis(trifluoromethanesulfonyl)imide, Dialkyl ((meth)acryloylamino, such as dialkyl((meth)acryloylaminoalkyl)sulfonium dicyanamide, dialkyl((meth)acryloylaminoalkyl)sulfonium thiocyanate, etc. An ionic liquid containing an alkyl) sulfonium cation.

On the other hand, the alkyl substituent is preferably an alkyl group having 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, and more preferably 1 to 6 carbon atoms.

As a quaternary phosphonium cationic liquid,

Trialkyl(vinyl)phosphonium bis(fluorosulfonyl)imide, trialkyl(vinyl)phosphonium bis(trifluoromethanesulfonyl)imide, trialkyl(vinyl)phosphonium dicyanamide, trialkyl Trialkyl (vinyl) phosphonium cation-containing ionic liquids such as (vinyl) phosphonium thiocyanate, etc.,

Trialkyl((meth)acryloyloxyalkyl)phosphonium bis(fluorosulfonyl)imide, trialkyl((meth)acryloyloxyalkyl)phosphonium bis(trifluoromethanesulfonyl)imide, Trialkyl ((meth)acryloyloxy, such as trialkyl((meth)acryloyloxyalkyl)phosphonium dicyanamide, trialkyl((meth)acryloyloxyalkyl)phosphonium thiocyanate, etc. Alkyl) phosphonium cation-containing ionic liquid,

Trialkyl((meth)acryloylaminoalkyl)phosphonium bis(fluorosulfonyl)imide, trialkyl((meth)acryloylaminoalkyl)phosphonium bis(trifluoromethanesulfonyl)imide, Trialkyl ((meth)acryloylamino, such as trialkyl((meth)acryloylaminoalkyl)phosphonium dicyanamide, trialkyl((meth)acryloylaminoalkyl)phosphonium thiocyanate, etc. Alkyl) phosphonium cation-containing ionic liquids.

On the other hand, the alkyl substituent is preferably an alkyl group having 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, and more preferably 1 to 6 carbon atoms.

In addition, as a quaternary ammonium cationic liquid,

N,N,N-trialkyl-N-vinylammonium tetrafluoroborate, N,N,N-trialkyl-N-vinylammonium trifluoroacetate, N,N,N-trialkyl-N-vinylammonium hepta Fluorobutyrate, N,N,N-trialkyl-N-vinylammonium trifluoromethanesulfonate, N,N,N-trialkyl-N-vinylammonium perfluorobutanesulfonate, N,N ,N-trialkyl-N-vinylammonium bis(trifluoromethanesulfonyl)imide, N,N,N-trialkyl-N-vinylammonium bis(pentafluoroethanesulfonyl)imide, N,N ,N-trialkyl-N-vinylammonium tris(trifluoromethanesulfonyl)imide, N,N,N-trialkyl-N-vinylammonium hexafluorophosphate, N,N,N-trialkyl-N -Vinylammonium (trifluoromethanesulfonyl)trifluoroacetamide, N,N,N-trialkyl-N-vinylammonium dicyanamide, N,N,N-trialkyl-N-vinylammonium thio N,N,N-trialkyl-N-vinylammonium cation-containing ionic liquids such as cyanate,

N,N,N-trialkyl-N-(meth)acryloyloxyalkylammonium tetrafluoroborate, N,N,N-trialkyl-N-(meth)acryloyloxyalkylammonium trifluoroacetate, N,N,N-trialkyl-N-(meth)acryloyloxyalkylammonium heptafluorobutyrate, N,N,N-trialkyl-N-(meth)acryloyloxyalkylammonium trifluoromethe Insulfonate, N,N,N-trialkyl-N-(meth)acryloyloxyalkylammonium perfluorobutanesulfonate, N,N,N-trialkyl-N-(meth)acryloyloxy Alkyl ammonium bis(trifluoromethanesulfonyl)imide, N,N,N-trialkyl-N-(meth)acryloyloxyalkylammonium bis(pentafluoroethanesulfonyl)imide, N,N, N-trialkyl-N-(meth)acryloyloxyalkylammonium tris(trifluoromethanesulfonyl)imide, N,N,N-trialkyl-N-(meth)acryloyloxyalkylammonium hexafluoro Lophosphate, N,N,N-trialkyl-N-(meth)acryloyloxyalkylammonium (trifluoromethanesulfonyl)trifluoroacetamide, N,N,N-trialkyl-N-(meth) ) N,N,N-trialkyl-N- such as acryloyloxyalkylammonium dicyanamide, N,N,N-trialkyl-N-(meth)acryloyloxyalkylammonium thiocyanate (Meth)acryloyloxyalkylammonium cation-containing ionic liquid,

N,N,N-trialkyl-N-(meth)acryloylaminoalkylammonium tetrafluoroborate, N,N,N-trialkyl-N-(meth)acryloylaminoalkylammonium trifluoroacetate, N,N,N-trialkyl-N-(meth)acryloylaminoalkylammonium heptafluorobutyrate, N,N,N-trialkyl-N-(meth)acryloylaminoalkylammonium trifluoromethe Insulfonate, N,N,N-trialkyl-N-(meth)acryloylaminoalkylammonium perfluorobutanesulfonate, N,N,N-trialkyl-N-(meth)acryloylamino Alkyl ammonium bis(trifluoromethanesulfonyl)imide, N,N,N-trialkyl-N-(meth)acryloylaminoalkylammonium bis(pentafluoroethanesulfonyl)imide, N,N, N-trialkyl-N-(meth)acryloylaminoalkylammonium tris(trifluoromethanesulfonyl)imide, N,N,N-trialkyl-N-(meth)acryloylaminoalkylammonium hexafluoro Lophosphate, N,N,N-trialkyl-N-(meth)acryloylaminoalkylammonium (trifluoromethanesulfonyl)trifluoroacetamide, N,N,N-trialkyl-N-(meth) ) N,N,N-trialkyl-N- such as acryloylaminoalkylammonium dicyanamide, N,N,N-trialkyl-N-(meth)acryloylaminoalkylammonium thiocyanate, etc. And (meth)acryloylaminoalkylammonium cation-containing ionic liquids.

On the other hand, the alkyl substituent is preferably an alkyl group having 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, and more preferably 1 to 6 carbon atoms.

Further, the reactive ionic liquid may be used without particular limitation, but it is more preferable that it is a reactive ionic liquid represented by the following general formulas 1 and/or 2. Polymer (B) containing a reactive ionic liquid represented by the following formula (1) and/or (2) as a monomer unit is suitably compatible with the polymer (A), and is more preferable in that it can suppress an increase in antistatic properties and high-speed peeling force. Do. In addition, since the reactive ionic liquid is a liquid (liquid) at any temperature within the range of 0 to 150°C, and is a nonvolatile molten salt, and has transparency, the obtained pressure-sensitive adhesive composition has antistatic properties (high conductivity) and heat resistance. (Thermal stability), transparency, and low fouling properties can be satisfied, so it is useful.

[Formula 1]

[Formula 2]

Meanwhile, in Formulas 1 and 2, R ¹ is a hydrogen atom or a methyl group, X ⁺ is a cation ^{moiety, and Y −} is an anion. Z represents a C1-C3 alkylene group.

^{As the cation moiety (X +} ) constituting the reactive ionic liquid represented by Formula 1 and/or 2, a quaternary ammonium group, imidazolium group, pyridinium group, piperidinium group, pyrrolidinium group, pyrrole group, agent A quaternary phosphonium group, a trialkylsulfonium group, a pyrazolium group, a guanidium group, etc. are mentioned. Among these, in particular, a quaternary ammonium group is excellent in transparency and is a preferred aspect for electron/optical applications. In addition, the quaternary ammonium group does not have unsaturated bonds other than polymerizable functional groups in the molecule, and it is difficult to inhibit the general radical polymerization reaction during ultraviolet (UV) curing, and it is presumed to have high curability. Suitable.

As the quaternary ammonium group, specifically, trimethylammonium group, triethylammonium group, tripropylammonium group, methyldiethylammonium group, ethyldimethylammonium group, methyldipropylammonium group, dimethylbenzyl ammonium group, diethylbenzylammonium group, methyldibenzyl Although an ammonium group, an ethyl dibenzyl ammonium group, etc. are mentioned, especially a trimethyl ammonium group and a methylbenzyl ammonium group are a preferable aspect from the point that it is easy to obtain an inexpensive industrial material.

Further, the anion (parts) (Y ^-) constituting the reactive ionic liquid represented by the formula 1 and / or 2, as the _{^{anion, SCN -, BF 4 -,}} PF 6 -, NO 3 -, CH 3 COO - _{^{, CF 3 COO -, CH 3}} SO 3 -, CF 3 SO 3 -, (FSO 2) 2 N -, (CF 3 SO 2) 2 N -, (CF 3 SO 2) 3 C -, AsF 6 -, _{^{SbF 6 -, NbF 6 -,}} TaF 6 -, F (HF) n -, (CN) 2 N -, C 4 F 9 SO 3 -, (C 2 F 5 SO 2) 2 N -, C 3 F 7 _{^{COO -, (CF 3 SO 2}} ) (CF 3 CO) N -, B (CN) 4 -, C (CN) 3 -, N (CN) 2 -, CH 3 OSO 3 -, C 2 H 5 OSO 3 _{^{-, C 4 H 9 OSO 3}} -, C 6 H 13 OSO 3 -, C 8 H 17 OSO 3 -, p- toluenesulfonate anion, a 2- (2-methoxyethyl) ethyl sulfate anion, (C ₂ F ₅ ) ₃ PF ₃ ^- and the like. In particular, an anion component containing a fluorine atom (a fluorine-containing anion) is preferable because an ionic liquid having a low melting point can be obtained and antistatic properties are excellent. On the other hand, as an anion, it is preferable not to use a chlorine ion, a bromine ion, etc. from the point of having corrosiveness.

As a combination of the cation (site) and anion (site) constituting the reactive ionic liquid represented by Formula 1 and/or 2, acryloylaminopropyltrimethylammonium bis(trifluoromethanesulfonyl) is particularly preferred. )Imide, methacryloylaminopropyltrimethylammonium bis(trifluoromethanesulfonyl)imide, acryloylaminopropyldimethylbenzylammonium bis(trifluoromethanesulfonyl)imide, acryloyloxy Ethyltrimethylammonium bis(trifluoromethanesulfonyl)imide, acryloyloxyethyldimethylbenzylammonium bis(trifluoromethanesulfonyl)imide, methacryloyloxyethyltrimethylammonium bis(trifluoro Lomethanesulfonyl)imide, acryloylaminopropyltrimethylammonium bis(fluorosulfonyl)imide, methacryloylaminopropyltrimethylammonium bis(fluorosulfonyl)imide, acryloylaminopropyl Dimethylbenzylammonium bis(fluorosulfonyl)imide, acryloyloxyethyltrimethylammonium bis(fluorosulfonyl)imide, acryloyloxyethyldimethylbenzylammonium bis(fluorosulfonyl)imide , Methacryloyloxyethyltrimethylammonium bis(fluorosulfonyl)imide, acryloylaminopropyltrimethylammonium trifluoromethanesulfonic acid, methacryloylaminopropyltrimethylammonium trifluoromethanesulfonic acid , Acryloylaminopropyldimethylbenzylammonium trifluoromethanesulfonic acid, acryloyloxyethyltrimethylammonium trifluoromethanesulfonic acid, acryloyloxyethyldimethylbenzylammonium trifluoromethanesulfonic acid, methacrylic Royloxyethyltrimethylammonium trifluoromethanesulfonic acid and the like.

Of the total structural units (total monomer units (components): 100% by mass) of the (meth)acrylic polymer, the reactive ionic liquid is preferably contained in an amount of 10 to 99% by mass, more preferably 15 to 98% by mass. And it is particularly preferable to contain 20 to 97% by mass. When the blending ratio of the reactive ionic liquid is within the above range, excellent antistatic properties, transparency, heat resistance (thermal stability), and low fouling properties can be exhibited, which is preferable.

As a general method for synthesizing a reactive ionic liquid, as long as the target ionic liquid is obtained, it is not particularly limited, but the document "Ionic liquid-the forefront and future of development -" [published by CMC Co., Ltd.], and the document "Polymer, Vol. 52, P. 1469-1482 (2011)", the quaternization/ion exchange method, direct quaternization method, carbonate ester as described in the document "Advanced Material System One Point 2 Ionic Liquid" [published by Kyoritsu Publishing Co., Ltd.] A quaternization method, a hydroxide method, an acid ester method, a complex formation method, and a neutralization method are used.

[(Meth)acrylic polymer (b)]

Hereinafter, the (meth)acrylic polymer (b), which is a suitable specific example of the polymer (B), will be described in detail.

As the (meth)acrylic polymer (b), an alkyl (meth)acrylate can be used, and it is a more preferable aspect to use an alkyl (meth)acrylate having an alkyl group having 1 to 14 carbon atoms. As said alkyl (meth)acrylate, 1 type or 2 or more types can be used.

Specific examples of the alkyl (meth)acrylate having an alkyl group having 1 to 14 carbon atoms include, for example, methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, and s-butyl (meth)acrylic. Rate, t-butyl (meth)acrylate, isobutyl (meth)acrylate, hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, n-octyl (meth)acrylate, isooctyl (meth) )Acrylate, n-nonyl (meth)acrylate, isononyl (meth)acrylate, n-decyl (meth)acrylate, isodecyl (meth)acrylate, n-dodecyl (meth)acrylate, n -Tridecyl (meth)acrylate, n-tetradecyl (meth)acrylate, etc. are mentioned.

It is preferable that the (meth)acrylic acid alkyl ester is contained in an amount of 0 to 90% by mass as a monomer unit (component) in the total structural units (total monomer units (components): 100% by mass) of the (meth)acrylic polymer (b). And it is more preferable to contain 30-85 mass %, and 50-80 mass% is still more preferable. If the monomer unit (component) is within the above range, it is preferable from the viewpoint of obtaining compatibility with the polymer (A).

In addition, as other polymerizable monomers other than the (meth)acrylate alkyl ester, for the purpose of modification such as cohesive strength and crosslinkability, if necessary, other polymerizable monomers that can be copolymerized with the (meth)acrylate alkyl ester You may contain the monomer unit (component) (copolymerizable monomer) you have.

It is preferable that the (meth)acrylic polymer (b) contains a monomer having a polyoxyalkylene skeleton as the copolymerizable monomer, and the monomer having a polyoxyalkylene skeleton is an average addition of oxyalkylene units It is more preferable that it is an alkylene oxide group-containing reactive monomer having 3 to 100 moles. When the (meth)acrylic polymer (b) contains a monomer having a polyoxyalkylene skeleton, it is preferable because the ionic conductivity of the reactive ionic liquid is improved.

In addition, in all the structural units (total monomer units (components): 100% by mass) of the (meth)acrylic polymer (b), an alkylene oxide group-containing reactive monomer having an average added mole number of 3 to 100 oxyalkylene units It is preferable to contain 1 to 80 mass %, and it is more preferable to contain 2 to 50 mass %. If the monomer unit (component) is within the above range, the ionic conductivity of the reactive ionic liquid is improved, which is preferable.

The average number of moles added of the oxyalkylene unit to the alkylene oxide group-containing reactive monomer is preferably 3 to 100, more preferably 4 to 80, and 5 to 50 from the viewpoint of compatibility with the polymer (A). It is particularly preferred. When the average number of added moles is 3 or more, the effect of reducing contamination of the adherend (to be protected) tends to be obtained efficiently. Further, when the average number of added moles is greater than 100, the interaction with the polymer (A) is large, and the pressure-sensitive adhesive composition tends to become a gel, making coating difficult, which is not preferable. On the other hand, the terminal of the oxyalkylene chain may be the hydroxyl group as it is, or may be substituted with another functional group or the like.

As the alkylene oxide group-containing reactive monomer, a monomer similar to that described in detail for the polymer (A) ((meth)acrylic polymer (a)) described above can be used.

In addition, as the monomer unit (copolymerizable monomer) having other polymerizable properties other than the alkylene oxide group-containing reactive monomer, the same as described in detail for the aforementioned polymer (A) ((meth)acrylic polymer (a)). Monomers (carboxyl group-containing monomers, hydroxyl group-containing monomers, polyfunctional monomers, etc.) can be used. On the other hand, the blending amount of the copolymerizable monomer is not particularly limited, but is preferably 0.1 to 50% by mass of the copolymerizable monomer based on the total amount of the monomer unit (component) for preparing the (meth)acrylic polymer (b). It is preferably 0.5 to 40% by mass, more preferably 1 to 30% by mass. By containing 0.1 mass% or more of the said copolymerizable monomer, a decrease in the cohesive force of the pressure-sensitive adhesive (adhesive layer, pressure-sensitive adhesive sheet) formed of the pressure-sensitive adhesive composition can be prevented, and contamination when peeled from the adherend can be prevented. Further, by setting the blending amount of the copolymerizable monomer to 50% by mass or less, a decrease in compatibility with the polymer (A) can be prevented, and an increase in high-speed adhesive strength can be suppressed.

The polymerization method of the polymer (B) ((meth)acrylic polymer (b)) containing the reactive ionic liquid used in the present invention as a monomer unit (component) is not particularly limited, and the aforementioned polymer (A) (( For the meth)acrylic polymer (a)), a method similar to that described in detail can be used. In addition, in the polymer obtained, similarly to the polymer (A) ((meth)acrylic polymer (a)) described above, any of a random copolymer, a block copolymer, an alternating copolymer, and a graft copolymer may be used. In addition, as for the polymerization initiator used at the time of polymerization, those similar to those described in detail for the polymer (A) ((meth)acrylic polymer (a)) described above can be used.

In addition, in order to adjust the intrinsic viscosity of the polymer (B) ((meth)acrylic polymer (b)), the same as the chain transfer agent described in detail in the above-described polymer (A) ((meth)acrylic polymer (a)) Can be used.

The blending amount of the chain transfer agent is not particularly limited, but usually 0.1 to 20 parts by mass of the chain transfer agent is preferred, more preferably 0.2 to 15 parts by mass, and still more preferably 0.3 to 10 parts by mass per 100 parts by mass of the monomer. . By adjusting the blending amount of the chain transfer agent in this way, a polymer (B) ((meth)acrylic polymer (b)) having a desired intrinsic viscosity can be obtained. On the other hand, the chain transfer agent may be used alone or in combination of two or more.

[Adhesive composition]

The pressure-sensitive adhesive composition of the present invention contains the aforementioned polymer (A) and polymer (B) as essential components.

The blending amount of the polymer (B) is preferably 0.05 to 30 parts by mass, more preferably 0.1 to 25 parts by mass, further preferably 0.5 to 20 parts by mass, particularly preferably based on 100 parts by mass of the polymer (A). It is 2.5 to 15 parts by mass. If the polymer (B) is blended (added) in excess of 30 parts by mass, the cohesive strength of the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition of the present invention is lowered, and contamination to the adherend may occur, which is not preferable. In addition, when the blending amount of the polymer (B) is less than 0.05 parts by mass, antistatic properties are not sufficient.

[Crosslinking agent]

As the crosslinking agent used when forming the pressure-sensitive adhesive layer, an isocyanate compound, an epoxy compound, a melamine resin, an aziridine derivative, an oxazoline crosslinking agent, a silicone crosslinking agent, a silane crosslinking agent, a metal chelate compound, and the like are used. Among them, mainly from the viewpoint of obtaining an appropriate cohesive force, an isocyanate compound or an epoxy compound is more preferably used, and particularly preferably an isocyanate compound (isocyanate-based crosslinking agent). These compounds may be used alone or in combination of two or more.

Examples of the isocyanate compound (isocyanate crosslinking agent) include lower aliphatic polyisocyanates such as butylene diisocyanate and hexamethylene diisocyanate, and cyclopentylene diisocyanate. Alicyclic isocyanates such as nate, cyclohexylene diisocyanate, and isophorone diisocyanate, 2,4-tolylene diisocyanate, 4,4'-diphenylmethane dia Aromatic isocyanates such as isocyanate and xylylene diisocyanate, trimethylolpropane/tolylenediisocyanate trimer adduct (trade name Coronate L, manufactured by Nippon Polyurethane Industrial Co., Ltd.) , Trimethylolpropane/hexamethylene diisocyanate trimer adduct (trade name Coronate HL, manufactured by Nippon Polyurethane Industrial Co., Ltd.), isocyanurate form of hexamethylene diisocyanate (trade name Coronate HX, Isocyanate adducts, such as Nippon Polyurethane Industrial Co., Ltd., etc. are mentioned. Alternatively, a compound having at least one isocyanate group and one or more unsaturated bonds in one molecule, specifically, 2-isocyanatoethyl (meth)acrylate, etc. may also be used as an isocyanate-based crosslinking agent. These compounds may be used alone or in combination of two or more.

Examples of the epoxy compound include bisphenol A, epichlorohydrin-type epoxy resin, ethylene glycidyl ether, polyethylene glycol diglycidyl ether, glycerin iglycidyl ether, and glycerin triglycidyl ether. , 1,6-hexanediolglycidyl ether, trimethylolpropane triglycidyl ether, diglycidylaniline, diamine glycidylamine, N,N,N',N'- Tetraglycidyl-m-xylenediamine (trade name TETRAD-X, manufactured by Mitsubishi Gas Chemical) or 1,3-bis(N,N-diglycidylaminomethyl)cyclohexane (trade name TETRAD-C, Mitsubishi Gas Chemical Co., Ltd.) etc. are mentioned. These compounds may be used alone or in combination of two or more.

Examples of the melamine resin include hexamethylol melamine. In addition, examples of the aziridine derivatives include commercially available products such as HDU (manufactured by Sogo Chemicals Corporation), brand names TAZM (manufactured by Sogos Plaster Corporation), and trade names TAZO (manufactured by Sogos Plaster Corporation). These compounds may be used alone or in combination of two or more.

Examples of the metal chelate compound include aluminum, iron, tin, titanium, nickel and the like as a metal component, and acetylene, methyl acetoacetate, and ethyl lactate as a chelate component. These compounds may be used alone or in combination of two or more.

The content of the crosslinking agent is preferably 0.01 to 30 parts by mass, more preferably 0.1 to 20 parts by mass, and more preferably 0.5 to 15 parts by mass based on 100 parts by mass of the polymer (A). It is more preferable, and it is particularly preferable to contain 0.5 to 10 parts by mass. When the content is less than 0.01 parts by mass, crosslinking formation by the crosslinking agent becomes insufficient, the cohesive force of the pressure-sensitive adhesive (layer) becomes small, and sufficient heat resistance may not be obtained. On the other hand, when the content exceeds 30 parts by mass, the crosslinking reaction proceeds in a short time to generate a gel-like foreign material in the pressure-sensitive adhesive composition, which tends to cause appearance defects.

Further, it is possible to contain a crosslinking catalyst for more effectively proceeding any of the aforementioned crosslinking reactions. As such a crosslinking catalyst, for example, a tin catalyst (especially dioctyl tin dilaurate) can be preferably used. The amount of the crosslinking catalyst (for example, a tin-based catalyst such as dioctyl tin dilaurate) is not particularly limited, but may be, for example, about 0.005 to 1 part by mass per 100 parts by mass of the polymer (A).

Further, in the present invention, as a crosslinking agent, a polyfunctional monomer having two or more radiation-reactive unsaturated bonds can be added. In this case, the pressure-sensitive adhesive composition is crosslinked by irradiation with radiation or the like. As a polyfunctional monomer having two or more radiation-reactive unsaturated bonds in a molecule, for example, one type or And a polyfunctional monomer component having two or more of two or more types of radiation reactive groups. In addition, as the polyfunctional monomer, in general, those having 10 or less radiation-reactive unsaturated bonds are suitably used. These compounds may be used alone or in combination of two or more.

Specific examples of the polyfunctional monomer having two or more radiation-reactive unsaturated bonds include, for example, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, neopentyl glycol Di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol hexa( Meth)acrylate, divinylbenzene, N,N'-methylenebisacrylamide, and the like.

The blending amount of the polyfunctional monomer is appropriately selected depending on the balance with the polymer (A) to be crosslinked. In order to obtain sufficient heat resistance, it is generally preferable to blend in an amount of 0.1 to 30 parts by mass per 100 parts by mass of the polymer (A). Further, from the viewpoint of flexibility, it is more preferable to blend in an amount of 10 parts by mass or less based on 100 parts by mass of the polymer (A).

Examples of the radiation include ultraviolet rays, laser rays, α-rays, β-rays, γ-rays, X-rays, electron rays, and the like, but ultraviolet rays are suitably used in terms of controllability and handling properties and cost. More preferably, ultraviolet rays having a wavelength of 200 to 400 nm are used. Ultraviolet rays can be irradiated using an appropriate light source such as a high-pressure mercury lamp, a microwave excitation lamp, and a chemical lamp. On the other hand, when ultraviolet rays are used as radiation, a photopolymerization initiator shown below can be added to the pressure-sensitive adhesive composition.

The photopolymerization initiator may be a substance that generates radicals or cations by irradiating ultraviolet rays with an appropriate wavelength that may trigger the polymerization reaction, depending on the kind of the radiation-reactive component.

As the photo-radical polymerization initiator, for example, benzoin, benzoin methyl ether, benzoin ethyl ether, o-benzoyl benzoic acid methyl-p-benzoin ethyl ether, benzoin isopropyl ether, α-methylbenzoin, etc. Acetophenones such as benzoin, benzyldimethyl ketal, trichloroacetophenone, 2,2-diethoxyacetophenone, 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methylpropiophenone, Propiophenones such as 2-hydroxy-4'-isopropyl-2-methylpropiophenone, benzophenone, methylbenzophenone, p-chlorobenzophenone, and benzophenones such as p-dimethylaminobenzophenone, 2 -Thioxanthones such as chlorothioxanthone, 2-ethylthioxanthone, and 2-isopropylthioxanthone, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, 2,4,6- Acylphosphine oxides such as trimethylbenzoyl diphenylphosphine oxide, (2,4,6-trimethylbenzoyl)-(ethoxy)-phenylphosphine oxide, benzyl, dibenzsuberone, α-acyloxime ester And the like. These compounds may be used alone or in combination of two or more.

In addition, as the photo cationic polymerization initiator, for example, onium salts such as aromatic diazonium salts, aromatic iodonium salts, and aromatic sulfonium salts, and organic metal complexes such as iron-allene complexes, titanocene complexes, and arylsilanol-aluminum complexes. Retention, nitrobenzyl ester, sulfonic acid derivative, phosphoric acid ester, phenol sulfonic acid ester, diazonaphthoquinone, N-hydroxyimidosulfonate, and the like. These compounds may be used alone or in combination of two or more.

The photopolymerization initiator is usually blended in an amount of 0.1 to 10 parts by mass with respect to 100 parts by mass of the polymer (A), and is preferably blended in a range of 0.2 to 7 parts by mass. If it is within the above range, it is easy to control the polymerization reaction, and it is preferable from the viewpoint of obtaining an appropriate molecular weight.

In addition, it is also possible to use photo-initiated polymerization aids such as amines in combination. Examples of the photo-initiating aid include 2-dimethylaminoethylbenzoate, dimethylaminoacetophenone, p-dimethylaminobenzoic acid ethyl ester, p-dimethylaminobenzoic acid isoamyl ester, and the like. These compounds may be used alone or in combination of two or more. It is preferable to mix|blend 0.05-10 mass parts with respect to 100 mass parts of polymer (A), and, as for a polymerization initiation aid, it is more preferable to mix|blend in the range of 0.1-7 mass parts. If it is within the above range, it is easy to control the polymerization reaction, and it is preferable from the viewpoint of obtaining an appropriate molecular weight.

When the photopolymerization initiator as an optional component is added as described above, the pressure-sensitive adhesive layer can be obtained by applying the pressure-sensitive adhesive composition to one side or both sides of a base film and then irradiating with light. Usually, a pressure-sensitive adhesive layer is obtained by photopolymerizing by irradiating ultraviolet rays having an illuminance of 1 to 200 mW/cm ² at a wavelength of 300 to 400 nm and a light amount of ^{about 200 to 4000 mJ/cm 2.}

It is preferable to further contain a conductive agent (antistatic agent) in the said adhesive composition. In particular, the conductive agent (antistatic agent) is more preferably an ionic compound or an ion conductive polymer, and more preferably an ionic compound such as an alkali metal salt or an ionic liquid. The ionic compound does not react with the reactive ionic liquid, can be contained as an additive separately, and can exhibit more excellent antistatic properties, which is a preferred embodiment. In addition, the ionic compound is preferable because it has high interactivity with the reactive ionic liquid incorporated in the skeleton of the polymer (B), suppresses the risk of bleeding out, and has excellent low fouling properties.

The content of the conductive agent used in the present invention is preferably 0 to 10 parts by mass, more preferably 0.01 to 5 parts by mass based on 100 parts by mass of the polymer (A) contained in the pressure-sensitive adhesive composition. And, it is more preferable to contain 0.1 to 3 parts by mass. When the content exceeds 10 parts by mass, bleeding out may occur, which is not preferable.

The pressure-sensitive adhesive composition may further contain a compound that generates ketoenol tautomerism. By containing the above compound, an effect of prolonging the pot life of the pressure-sensitive adhesive composition can be realized by suppressing an increase in excessive viscosity or gelation of the pressure-sensitive adhesive composition after the crosslinking agent is blended. When at least an isocyanate compound is used as the crosslinking agent, it is particularly meaningful to contain a compound that generates ketoenol tautomerism. This technique can be preferably applied, for example, when the pressure-sensitive adhesive composition is in the form of an organic solvent solution or a non-solvent.

As the compound generating the ketoenol tautomerism, various β-dicarbonyl compounds can be used. As a specific example, acetylacetone, 2,4-hexanedione, 3,5-heptanedione, 2-methylhexane-3,5-dione, 6-methylheptane-2,4-dione, Β-diketones such as 2,6-dimethylheptane-3,5-dione; Acetoacetic acid esters such as methyl acetoacetate, ethyl acetoacetate, isopropyl acetoacetate, and tert-butyl acetoacetate; Propionyl acetate esters such as propionyl ethyl acetate, propionyl ethyl acetate, propionyl acetate isopropyl, and propionyl acetate tert-butyl; Isobutyryl acetic acid esters such as isobutyryl ethyl acetate, isobutyryl ethyl acetate, isobutyl isobutyl acetate, and tert-butyl isobutyryl acetate; Malonic acid esters, such as methyl malonate and ethyl malonate, etc. are mentioned. Among them, preferred compounds include acetylacetone and acetoacetic acid esters. The compounds generating such ketoenol tautomerism may be used alone or in combination of two or more.

The content of the compound that generates ketoenol tautomerism may be, for example, 0.1 to 20 parts by mass, more preferably 0.5 to 15 parts by mass, further preferably 1 to 10 parts by mass, based on 100 parts by mass of the polymer (A). It can be done in parts by mass. When the content of the compound is less than 0.1 parts by mass, it may be difficult to exhibit a sufficient effect of use. On the other hand, when the amount of the compound exceeds 20 parts by mass, it may remain in the pressure-sensitive adhesive layer to lower the antistatic property.

In addition, the pressure-sensitive adhesive composition may contain other known additives, such as powders such as colorants and pigments, surfactants, plasticizers, tackifiers, low molecular weight polymers, surface lubricants, leveling agents, antioxidants, corrosion inhibitors , A light stabilizer, an ultraviolet absorber, a polymerization inhibitor, a silane coupling agent, an inorganic or organic filler, a metal powder, a particulate matter, a thin material, and the like can be appropriately added depending on the application.

The pressure-sensitive adhesive composition is based on a liquid composition (adhesive composition, pressure-sensitive adhesive solution) in which the polymer (A) and polymer (B), and other components (crosslinking agent, conductive agent, etc.) used as necessary are dispersed or dissolved in a suitable solvent. It is a preferred aspect to be obtained by forming on at least one side of the film. For example, a method of applying the liquid composition (adhesive composition, pressure-sensitive adhesive solution) to one side of a base film, drying it, and performing curing treatment (heat treatment, ultraviolet treatment, etc.) as necessary can be preferably employed.

As the solvent constituting the pressure-sensitive adhesive composition, it is preferable that the component (raw material) used when forming the pressure-sensitive adhesive layer can be stabilized and dissolved or dispersed. As such a solvent, an organic solvent, water, or a mixed solvent thereof can be used. Examples of the organic solvent include esters such as ethyl acetate, butyl acetate, and 2-hydroxyethyl acetate; Ketones such as methyl ethyl ketone, acetone, cyclohexanone, methyl isobutyl ketone, diethyl ketone, methyl-n-propyl ketone, and acetylacetone; Cyclic ethers such as tetrahydrofuran (THF) and dioxane; aliphatic or alicyclic hydrocarbons such as n-hexane and cyclohexane; Aromatic hydrocarbons such as toluene and xylene; Aliphatic or alicyclic alcohols such as methanol, ethanol, n-propanol, isopropanol, and cyclohexanol; Glycol ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, and diethylene glycol monoethyl ether; One or two or more selected from glycol ether acetates such as diethylene glycol monomethyl ether acetate and diethylene glycol monoethyl ether acetate can be used.

The coating and coating of the pressure-sensitive adhesive composition can be performed using a conventional coater such as a gravure roll coater, a reverse roll coater, a kiss roll coater, a dip roll coater, a bar coater, a knife coater, and a spray coater. On the other hand, the pressure-sensitive adhesive composition may be directly applied to the base film to form a pressure-sensitive adhesive layer, or the pressure-sensitive adhesive layer formed on the release liner may be transferred to the substrate.

[Adhesive layer]

It is preferable that the pressure-sensitive adhesive layer of the present invention is formed of the pressure-sensitive adhesive composition. Since the pressure-sensitive adhesive composition is used, the obtained pressure-sensitive adhesive layer is excellent in antistatic properties, adhesiveness, re-peelability, and transparency.

The pressure-sensitive adhesive layer has a gel fraction (solvent insoluble fraction) of 85.00 to 99.95 mass%, more preferably 86.00 to 99.00 mass%. If the gel fraction (solvent insoluble fraction) is less than 85.00% by mass, the cohesive force will be insufficient and may be contaminated when peeled from the adherend (to be protected), and if the gel fraction exceeds 99.95% by mass, the cohesive force will be too high, and Sufficient adhesive strength (high-speed peeling force, low-speed peeling force) may be inferior. In addition, the evaluation method of the gel fraction will be described later.

The thickness of the pressure-sensitive adhesive layer is not particularly limited, but in general, good adhesion can be achieved by, for example, 3 to 100 µm, preferably 5 to 80 µm, and more preferably 10 to 50 µm. If the thickness of the pressure-sensitive adhesive layer is less than 3 μm, the adhesiveness may be insufficient, and lifting or peeling may occur, while if the thickness of the pressure-sensitive adhesive layer exceeds 100 μm, high-speed peeling force increases and the peeling workability decreases. There is.

The pressure-sensitive adhesive sheet of the present invention is provided with a pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition on at least one side of a base film. The pressure-sensitive adhesive sheet is provided with such a pressure-sensitive adhesive layer fixedly on at least one side of a base film, that is, without intention of separating the pressure-sensitive adhesive layer from the base film. The concept of the pressure-sensitive adhesive sheet referred to herein may include what is referred to as an adhesive tape, an adhesive film, an adhesive label, or the like. Further, depending on the intended use, it may be cut into an appropriate shape, punched, or the like. On the other hand, the pressure-sensitive adhesive layer is not limited to being continuously formed, and may be, for example, a pressure-sensitive adhesive layer formed in a regular or random pattern such as a dot shape or a stripe shape.

In addition, it is possible to bond a release liner to the pressure-sensitive adhesive layer surface for the purpose of protecting the pressure-sensitive adhesive surface as necessary to the pressure-sensitive adhesive sheet of the present invention, the surface protective sheet described later, and the optical surface protective sheet.

As a material constituting the release liner, for example, paper or a plastic film is used, but a plastic film is suitably used in view of excellent surface smoothness. The film is not particularly limited as long as it is a film capable of protecting the pressure-sensitive adhesive layer, and for example, a polyethylene film, a polypropylene film, a polybutene film, a polybutadiene film, a polymethylpentene film, a polyvinyl chloride film, a vinyl chloride A copolymer film, a polyethylene terephthalate film, a polybutylene terephthalate film, a polyurethane film, an ethylene-vinyl acetate copolymer film, etc. are mentioned.

The thickness of the release liner is usually 5 µm to 200 µm, preferably about 10 µm to 100 µm. If it is within the above range, it is preferable because the bonding workability to the pressure-sensitive adhesive layer and the peeling workability from the pressure-sensitive adhesive layer are excellent. The release liner may be subjected to a release and antifouling treatment with a silicone-based, fluorine-based, long-chain alkyl-based or fatty acid amide-based release agent, silica powder, or the like, or antistatic treatment such as a coating type, a lead-in type, and a vapor deposition type, if necessary. .

[Substrate film]

As the base film, for example

Polyethylene, polypropylene, poly-1-butene, poly-4-methyl-1-pentene, ethylene/propylene copolymer, ethylene/1-butene copolymer, ethylene/vinyl acetate copolymer, ethylene/ethyl acrylate copolymer, Polyolefin film such as ethylene/vinyl alcohol copolymer, polyester film such as polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate, polyacrylate film, polystyrene film, nylon 6, nylon 6,6, partially aromatic polyamide Plastic films such as polyamide films, polyvinyl chloride films, polyvinylidene chloride films, and polycarbonate films;

Foam base materials such as polyurethane foam and polyethylene foam;

Paper such as kraft paper, crepe paper, and Japanese paper;

Fabrics such as cotton cloth and staple fiber cloth;

Nonwoven fabrics such as polyester nonwoven fabric and vinylon nonwoven fabric;

Metal foil such as aluminum foil and copper foil

Etc. can be appropriately selected and used according to the use of the adhesive tape. When using the pressure-sensitive adhesive sheet of the present invention as a surface protection sheet described later, it is preferable to use a plastic film such as a polyolefin film, a polyester film, and a polyvinyl chloride film as the base film. Moreover, especially when using as an optical surface protection sheet, it is preferable to use a polyolefin film, a polyethylene terephthalate film, a polybutylene terephthalate film, and a polyethylene naphthalate film. As the plastic film, any of a non-stretched film and a stretched (uniaxially stretched or biaxially stretched) film can be used.

In addition, the base film includes, if necessary, a release agent of a silicone-based, fluorine-based, long-chain alkyl-based or fatty acid amide-based, silica powder, etc., and an antifouling treatment or acid treatment, alkali treatment, primer treatment, corona treatment, plasma treatment, ultraviolet rays. It is also possible to perform an electrostatic treatment such as an easy adhesion treatment such as a treatment, an application type, a lead-in type, and an evaporation type.

The thickness of the base film can be appropriately selected depending on the purpose, but is generally about 5 µm to 200 µm (typically 10 µm to 100 µm).

In addition, as the plastic film used for the base film used for the pressure-sensitive adhesive sheet of the present invention, it is more preferable to use a plastic film obtained by antistatic treatment. The generation of static electricity can be prevented by performing antistatic treatment, and it is useful in the technical field related to optical and electronic parts where charging becomes a particularly serious problem. The antistatic treatment applied to the plastic film is not particularly limited, but a method of providing an antistatic layer on at least one side of a generally used film or a method of incorporating an integrated antistatic agent into a plastic film is used. As a method of providing an antistatic layer on at least one side of the film, a method of applying an antistatic resin or a conductive polymer composed of an antistatic agent and a resin component, a conductive resin containing a conductive material, or a method of depositing or plating a conductive material. I can.

Examples of the antistatic agent contained in the antistatic resin include cationic antistatic agents having cationic functional groups such as quaternary ammonium salts, pyridinium salts, first, second, and third amino groups, sulfonates or sulfuric ester salts, and phosphonates. Anionic antistatic agents having anionic functional groups such as fonates and phosphate ester salts, alkyl betaine and derivatives thereof, imidazoline and derivatives thereof, amphoteric antistatic agents such as alanine and derivatives thereof, amino alcohol and derivatives thereof, glycerin and Derivatives thereof, nonionic antistatic agents such as polyethylene glycol and derivatives thereof, and further, ion conductive polymers obtained by polymerization or copolymerization of a monomer having an ion conductive group of the cationic, anionic, and amphoteric ionic types can be mentioned. . These compounds may be used alone or in combination of two or more.

Specifically, as the cationic antistatic agent, for example, 4 such as alkyl trimethyl ammonium salt, acyloylamidopropyl trimethyl ammonium methosulfate, alkylbenzylmethyl ammonium salt, choline acyl chloride, polydimethylaminoethyl methacrylate, etc. (Meth)acrylate copolymer having a quaternary ammonium group, styrene copolymer having a quaternary ammonium group such as polyvinylbenzyltrimethylammonium chloride, diallylamine copolymer having a quaternary ammonium group such as polydiallyldimethylammonium chloride And the like. These compounds may be used alone or in combination of two or more.

Examples of the anionic antistatic agent include an alkyl sulfonate, an alkylbenzene sulfonate, an alkyl sulfuric acid ester salt, an alkylethoxysulfuric acid ester salt, an alkyl phosphoric acid ester salt, and a sulfonic acid group-containing styrene copolymer. These compounds may be used alone or in combination of two or more.

Examples of the amphoteric antistatic agent include alkyl betaine, alkyl imidazolium betaine, and carbo betaine graft copolymerization. These compounds may be used alone or in combination of two or more.

As the nonionic antistatic agent, for example, fatty acid alkylolamide, di (2-hydroxyethyl) alkylamine, polyoxyethylene alkylamine, fatty acid glycerin ester, polyoxyethylene glycol fatty acid ester, sorbitan fatty acid ester, polyoxy Sorbitan fatty acid ester, polyoxyethylene alkylphenyl ether, polyoxyethylene alkyl ether, polyethylene glycol, polyoxyethylenediamine, polyether, polyester and polyamide copolymer, methoxypolyethylene glycol (meth) Acrylate, etc. are mentioned. These compounds may be used alone or in combination of two or more.

Examples of the conductive polymer include polyaniline, polypyrrole, and polythiophene.

Examples of the conductive material include tin oxide, antimony oxide, indium oxide, cadmium oxide, titanium oxide, zinc oxide, indium, tin, antimony, gold, silver, copper, aluminum, nickel, chromium, titanium, iron, cobalt, copper iodide. And alloys or mixtures thereof.

As the resin component used for the antistatic resin and the conductive resin, general-purpose resins such as polyester, acrylic, polyvinyl, urethane, melamine, and epoxy are used. On the other hand, in the case of a polymer type antistatic agent, it is not necessary to contain a resin component. In addition, it is also possible to contain compounds such as methylolated or alkylolated melamine-based, urea-based, glyoxal-based and acrylamide-based compounds, epoxy compounds, and isocyanate-based compounds as a crosslinking agent in the antistatic resin component.

As a method of forming the antistatic layer, for example, the antistatic resin, conductive polymer, and conductive resin are diluted with an organic solvent or a solvent such as water, and the coating solution is applied to a plastic film and dried.

Examples of the organic solvent used to form the antistatic layer include methyl ethyl ketone, acetone, ethyl acetate, tetrahydrofuran, dioxane, cyclohexanone, n-hexane, toluene, xylene, methanol, ethanol, n-propanol, Isopropanol and the like. These solvents may be used alone or in combination of two or more.

As for the coating method in the formation of the antistatic layer, a known coating method is appropriately used, and specifically, for example, roll coating, gravure coating, reverse coating, roll brush, spray coating, air knife coating, impregnation and curtain coating method Can be mentioned.

The thickness of the antistatic resin layer, the conductive polymer and the conductive resin is usually 0.01 µm to 5 µm, preferably about 0.03 µm to 1 µm.

Examples of the method of vapor deposition or plating of the conductive material include vacuum vapor deposition, sputtering, ion plating, chemical vapor deposition, spray pyrolysis, chemical plating, and electroplating.

The thickness of the conductive material layer is usually 2 nm to 1000 nm, preferably 5 nm to 500 nm.

In addition, as the lead-in type antistatic agent, the antistatic agent is suitably used. As the blending amount of the lead-in antistatic agent, it is used in the range of 20% by mass or less, preferably 0.05 to 10% by mass with respect to the total mass of the plastic film. As the blending method, any method in which the antistatic agent can be uniformly mixed with the resin used in the plastic film is not particularly limited, and for example, a heating roll, a Banbury mixer, a pressure kneader, a twin-screw kneader, or the like is used.

[Adhesive sheet]

The pressure-sensitive adhesive sheet of the present invention has a characteristic (adhesiveness) that the adhesive force at the time of high-speed peeling is small (removable property), and the adhesive force at the time of low-speed peeling is sufficiently high so that a problem such as lifting or peeling does not occur.

The adhesive strength at the time of the low-speed peeling can be evaluated by a 180° peeling (peel) adhesion test when peeling at a tensile speed of 0.3 m/min (low speed) and a peeling angle of 180°, and if it is 0.04 N/25 mm or more It is judged to be good. The 180° peel adhesion is more preferably 0.06 N/25 mm or more, and still more preferably 0.08 N/25 mm or more. In addition, the upper limit of the 180° peel adhesion is not particularly required, but is usually 1.0 N/25 mm or less. The detailed conditions of the 180° peel adhesion test are measured in accordance with the methods and conditions described in Examples to be described later.

The adhesive force at the time of the high-speed peeling can be evaluated by a 180° peeling (peeling) adhesion test when peeling at a tensile speed of 30 m/min (high speed) and a peeling angle of 180°, and it is judged to be good if it is 10 N/25 mm or less. The 180° peel adhesion is more preferably 9N/25mm or less, and still more preferably 7N/25mm or less. In addition, the lower limit of the 180° peel adhesion is not particularly required, but is usually 0.05 N/25 mm or more. The 180° peel adhesion test is measured according to the method and conditions described in Examples to be described later.

Further, the pressure-sensitive adhesive sheet of the present invention has a property of excellent antistatic properties. As the peeling electrification voltage in the pressure-sensitive adhesive sheet of the present invention, an absolute value of 1.0 kV or less is preferable, 0.8 kV or less is more preferable, and 0.6 kV or less is particularly preferable. Within the above range, it is possible to collect dust by static electricity or prevent electrostatic damage to electronic components, and is useful. The detailed conditions of the peeling electrification voltage measurement are measured according to the method and conditions described in Examples to be described later.

In addition, the pressure-sensitive adhesive sheet of the present invention has a property of high transparency. The transparency of the pressure-sensitive adhesive sheet of the present invention can be evaluated by haze, and in particular, it is judged to be good if the haze is less than 10%. Haze is more preferably less than 8.5%, and still more preferably less than 7%. The detailed conditions of haze measurement are measured according to the method and conditions described in Examples to be described later.

Since the pressure-sensitive adhesive sheet of the present invention has the above-described characteristics, it can be used as a pressure-sensitive adhesive sheet for re-peel and an anti-static pressure-sensitive adhesive sheet in particular utilizing adhesiveness, re-peelability and antistatic properties.

In addition, utilizing the above characteristics, it is commercially used as a surface protection sheet (film) used for the purpose of protecting the surface of an optical member such as a polarizing plate, a wavelength plate, an optical compensation film, and a reflective sheet. It can also be used as an optical film with a surface protection sheet in which the optical surface protection sheet is attached to the optical member.

In addition, as the adherend (to be protected) to which the surface protection sheet can be applied, PE (polyethylene), PP (polypropylene), ABS (acrylonitrile-butadiene-styrene copolymer), SBS (styrene) -A variety of resins including acrylic resins such as butadiene-styrene block copolymer), PC (polycarbonate), PVC (vinyl chloride), PMMA (polymethyl methacrylate resin), or SUS (stainless steel), aluminum Automobiles (the body coating film), main building materials, home appliances, etc. using members made of metal such as metal or glass, etc. are mentioned.

Moreover, when using the adhesive sheet of this invention as a surface protection sheet, the said adhesive sheet can be used as it is. However, especially when used as a sheet for surface protection, it is preferable to use a polyolefin film, a polyester film, and a polyvinyl chloride film of 10 micrometers-100 micrometers as a base film from a viewpoint of prevention of scratches and contamination and processability. In addition, the thickness of the pressure-sensitive adhesive layer is preferably about 3 to 50 µm.

In addition, in addition to the above adhesive properties, the pressure-sensitive adhesive sheet of the present invention is preferably used as a surface protection sheet for optics used for surface protection of an optical film because of the property of particularly high transparency. As an optical film to which the optical surface protection sheet of the present invention can be applied, a polarizing plate used in image display devices such as liquid crystal displays, plasma displays, and organic EL displays, wavelength plates, optical compensation films, light diffusion sheets, reflective sheets, and antireflection A sheet, a brightness improving film, a transparent conductive film (ITO film), etc. are mentioned.

The pressure-sensitive adhesive sheet of the present invention is used in the manufacturing process of a display device (liquid crystal module) in a manufacturing process of a display device (liquid crystal module) in a manufacturer of an optical film such as the polarizing plate, for protection when shipping an optical film, or in a manufacturer of an image display device such as a liquid crystal display. It can be used for the protection use of an optical film, etc., furthermore, for the protection use of an optical film in various processes, such as punching and cutting processing.

When using the pressure-sensitive adhesive sheet of the present invention as an optical surface protection sheet, the pressure-sensitive adhesive sheet can be used as it is. However, especially when used as a surface protection sheet for an optical film, from the viewpoint of prevention of scratches and contamination, processability, and transparency, the base film is a polyolefin film of 10 µm to 100 µm, a polyethylene terephthalate film, a polybutylene terephthalate film, It is preferable to use a polyethylene naphthalate film. In addition, the thickness of the pressure-sensitive adhesive is preferably about 3 µm to 40 µm.

[Optical film with adhesive sheet]

Moreover, it is preferable that the optical film of this invention is an optical film with a pressure-sensitive adhesive sheet to which the said pressure-sensitive adhesive sheet (surface protection sheet for optical) is attached. The optical film with a pressure-sensitive adhesive sheet of the present invention is obtained by attaching the pressure-sensitive adhesive sheet (optical surface protection sheet) to one or both surfaces of an optical film. The optical film with an adhesive sheet of the present invention is a manufacturing process of a display device (liquid crystal module) in a manufacturer of optical films such as the polarizing plate, when shipping an optical film, or in a manufacturer of an image display device such as a liquid crystal display device. In addition, in various processes such as punching or cutting, it is possible to prevent the optical film from being scratched and from adhering dust or dust. Moreover, since the transparency of the optical surface protection sheet is high, it is possible to perform inspection as it is. Moreover, when it becomes unnecessary, the optical surface protection sheet can be peeled off easily without damaging an optical film or an image display device.

Example

Hereinafter, the present invention will be described in detail based on examples, but the present invention is not limited at all by these examples. On the other hand, the components of the pressure-sensitive adhesive compositions according to Examples 1 to 10 and Comparative Examples 1 to 2 are shown in Table 1, and the evaluation results are shown in Table 2. In addition, "parts" and "%" in the following description are based on mass, unless otherwise specified.

<Polymer (A): Preparation of (meth)acrylic polymer (a)>

To a four-necked flask equipped with a stirring blade, thermometer, nitrogen gas introduction tube, cooler, and dropping funnel, 96 parts by mass of 2-ethylhexyl acrylate (2EHA), 4 parts by mass of 2-hydroxyethyl acrylate (HEA), thermal polymerization initiator 0.2 parts by mass of 2,2′-azobisisobutyronitrile and 150 parts by mass of ethyl acetate were added, nitrogen gas was introduced while stirring slowly, and the liquid temperature in the flask was maintained at around 65°C, and a polymerization reaction was carried out for 6 hours. , (Meth)acrylic polymer (a) solution (40 mass%) was prepared. The glass transition temperature calculated from the Fox formula of this (meth)acrylic polymer (a) was -68°C and a weight average molecular weight of 550,000.

<Preparation of reactive ionic liquid (DMAEA-TFSI)>

Ion 114 parts of potassium bis(trifluoromethanesulfonyl)imide while stirring 100 parts of a 79% aqueous solution of 2-(acryloyloxy)ethyltrimethylammonium chloride (DMAEA-Q manufactured by Kojin Co., Ltd.) in a 1 L three-necked flask. What diluted in 80 parts of exchanged water was added under heating at 60 degreeC. After 2 hours, the oil layer portion of the lower layer separated by two layers was taken out, washed three times with ion-exchanged water, and traced moisture remaining under reduced pressure was removed, and 2-(acryloyloxy)ethyltrimethylammonium bis( Trifluoromethanesulfonyl)imide (DMAEA-TFSI) was obtained.

<Preparation of reactive ionic liquid (DMAPAA-TFSI)>

While stirring 100 parts of a 75% aqueous solution of (3-acrylamidepropyl) trimethylammonium chloride (DMAPAA-Q manufactured by Gojin Co., Ltd.) in a 1 L three-necked flask, 116 parts of potassium bis(trifluoromethanesulfonyl)imide is ion-exchanged. What diluted in 80 parts was added under heating at 60 degreeC. After 2 hours, the oil layer portion of the lower layer separated by two layers was taken out, washed three times with ion-exchanged water, and then trace moisture remaining under reduced pressure was removed, and (3-acrylamidepropyl) trimethylammonium bis(trifluoro). Rometeinsulfonyl)imide (DMAPAA-TFSI) was obtained.

<Polymer (B): Preparation of (meth)acrylic polymer (b1)>

150 parts by mass of ethyl acetate, 20 parts by mass of acryloxyethyltrimethylammonium bis(trifluoromethanesulfonyl)imide (DMAEA-TFSI), 80 parts by mass of 2-ethylhexyl acrylate, and α-thio as a chain transfer agent 3.5 parts by mass of glycerol was put into a four-necked flask equipped with a stirring blade, a thermometer, a nitrogen gas introduction tube, a cooler, and a dropping funnel. Then, after stirring for 1 hour in a nitrogen atmosphere at 70°C, 0.2 parts by mass of 2,2'-azobisisobutyronitrile as a thermal polymerization initiator was added, followed by reaction at 70°C for 2 hours, and then 5 at 80°C. It was allowed to react for time. The intrinsic viscosity of the obtained (meth)acrylic polymer (b1) was 0.032 (dL/g).

<Polymer (B): Preparation of (meth)acrylic polymer (b2)>

Ethyl acetate 150 parts by mass, acryloxyethyltrimethylammonium bis(trifluoromethanesulfonyl)imide (DMAEA-TFSI) 20 parts by mass, methoxypolyethylene glycol methacrylate having an average added mole number of 23 oxyethylene units ( Brand name: BLEMMER PME-1000, manufactured by Nichiyu Corporation) 20 parts by mass, 2-ethylhexyl acrylate 60 parts by mass, and α-thioglycerol 3.5 parts by mass as a chain transfer agent, stirring blade, thermometer, nitrogen gas introduction pipe, cooler , Into a four-necked flask equipped with a dropping funnel. Then, after stirring for 1 hour in a nitrogen atmosphere at 70°C, 0.2 parts by mass of 2,2'-azobisisobutyronitrile as a thermal polymerization initiator was added, followed by reaction at 70°C for 2 hours, and then 5 at 80°C. It was allowed to react for time. The intrinsic viscosity of the obtained (meth)acrylic polymer (b2) was 0.041 (dL/g).

<Polymer (B): Preparation of (meth)acrylic polymer (b3)>

233 parts by mass of ethyl acetate, 20 parts by mass of acryloxyethyltrimethylammonium bis(trifluoromethanesulfonyl)imide (DMAEA-TFSI), methoxypolyethylene glycol methacrylate having an average added mole number of 23 in oxyethylene units ( Brand name: BLEMMER PME-1000, manufactured by Nichiyu Corporation) 20 parts by mass, 2-ethylhexyl acrylate 60 parts by mass, and 3.5 parts by mass of methyl thioglycolate as a chain transfer agent, stirring blade, thermometer, nitrogen gas introduction pipe, cooler , Into a four-necked flask equipped with a dropping funnel. Then, after stirring for 1 hour in a nitrogen atmosphere at 70°C, 0.2 parts by mass of 2,2'-azobisisobutyronitrile as a thermal polymerization initiator was added, followed by reaction at 70°C for 2 hours, and then 5 at 80°C. It was allowed to react for time. The intrinsic viscosity of the obtained (meth)acrylic polymer (b3) was 0.039 (dL/g).

<Polymer (B): Preparation of (meth)acrylic polymer (b4)>

Ethyl acetate 150 parts by mass, (3-acrylamidepropyl) trimethylammonium bis(trifluoromethanesulfonyl) imide (DMAPAA-TFSI) 20 parts by mass, methoxypolyethylene glycol having an average added mole number of 23 oxyethylene units Methacrylate (trade name: BLEMMER PME-1000, manufactured by Nichiyu Corporation) 20 parts by mass, 2-ethylhexyl acrylate 60 parts by mass, and α-thioglycerol 3.5 parts by mass as a chain transfer agent stirring blade, thermometer, nitrogen gas It was put into a four-necked flask equipped with an introduction tube, a cooler, and a dropping funnel. Then, after stirring for 1 hour in a nitrogen atmosphere at 70°C, 0.2 parts by mass of 2,2'-azobisisobutyronitrile as a thermal polymerization initiator was added, followed by reaction at 70°C for 2 hours, and then 5 at 80°C. It was allowed to react for time. The intrinsic viscosity of the obtained (meth)acrylic polymer (b4) was 0.045 (dL/g).

<Polymer (B): Preparation of (meth)acrylic polymer (b5)>

233 parts by mass of ethyl acetate, (3-acrylamidepropyl) trimethylammonium bis(trifluoromethanesulfonyl) imide (DMAPAA-TFSI) 20 parts by mass, methoxypolyethylene glycol having an average added mole number of 23 oxyethylene units Methacrylate (trade name: Blemmer PME-1000, manufactured by Nichiyu Corporation) 20 parts by mass, 2-ethylhexyl acrylate 60 parts by mass, and methyl thioglycolate 3.5 parts by mass as a chain transfer agent Stirring blade, thermometer, nitrogen gas It was put into a four-necked flask equipped with an introduction tube, a cooler, and a dropping funnel. Then, after stirring for 1 hour in a nitrogen atmosphere at 70°C, 0.2 parts by mass of 2,2'-azobisisobutyronitrile as a thermal polymerization initiator was added, followed by reaction at 70°C for 2 hours, and then 5 at 80°C. It was allowed to react for time. The intrinsic viscosity of the obtained (meth)acrylic polymer (b5) was 0.043 (dL/g).

[Example 1]

(Preparation of adhesive composition)

To 500 parts by mass of a solution obtained by diluting the (meth)acrylic polymer (a) solution (35% by mass) to 20% by mass with ethyl acetate (100 parts by mass of the polymer), 25 parts by mass (solid content) of the (meth)acrylic polymer (b1) 40% by mass ethyl acetate solution), as a crosslinking agent, coronate L (75% by weight solid content of trimethylolpropane/tolylenediisocyanate trimer adduct, ethyl acetate solution, manufactured by Nippon Polyurethane Industrial Co., Ltd.) 4.0 parts by mass, crosslinking As a catalyst, 3.0 parts by mass of dioctyl tin dilaurate (1% by weight ethyl acetate solution) was added, followed by mixing and stirring at 25°C for about 5 minutes to prepare a pressure-sensitive adhesive composition (1).

(Production of adhesive sheet)

The pressure-sensitive adhesive composition (1) was applied to a surface opposite to the antistatic treatment surface of a polyethylene terephthalate film with an antistatic treatment layer (trade name: Diafoil T100G38, manufactured by Mitsubishi Resin Co., Ltd., thickness 38㎛), and 2 at 130°C. It heated for a minute to form a pressure-sensitive adhesive layer having a thickness of 15 µm.

Next, to the surface of the pressure-sensitive adhesive layer, a silicone-treated surface of a 25 µm-thick polyethylene terephthalate film subjected to silicone treatment on one side was bonded to each other to prepare a pressure-sensitive adhesive sheet.

[Example 2]

(Preparation of adhesive composition)

Except for using 3.8 parts by mass of the (meth)acrylic polymer (b2) (40 parts by mass ethyl acetate solution) in place of 25 parts by mass of the (meth)acrylic polymer (b1) (solid content 40% by mass ethyl acetate solution), It carried out similarly to Example 1, and prepared the adhesive composition (2).

(Production of adhesive sheet)

A pressure-sensitive adhesive sheet was produced in the same manner as in Example 1, except that the pressure-sensitive adhesive composition (2) was used instead of the pressure-sensitive adhesive composition (1).

[Example 3]

(Preparation of adhesive composition)

In place of the (meth)acrylic polymer (b1) 25 parts by mass (solid content 40% by mass ethyl acetate solution), except for using 8.3 parts by mass of the (meth)acrylic polymer (b3) (solid content 30% by mass ethyl acetate solution), It carried out similarly to Example 1, and prepared the adhesive composition (3).

(Production of adhesive sheet)

A pressure-sensitive adhesive sheet was produced in the same manner as in Example 1, except that the pressure-sensitive adhesive composition (3) was used instead of the pressure-sensitive adhesive composition (1).

[Example 4]

(Preparation of adhesive composition)

In place of the (meth)acrylic polymer (b1) 25 parts by mass (solid content 40% by mass ethyl acetate solution), except for using 12.5 parts by mass (solid content 40% by mass ethyl acetate solution) of the (meth)acrylic polymer (b2), It carried out similarly to Example 1, and prepared the adhesive composition (4).

(Production of adhesive sheet)

A pressure-sensitive adhesive sheet was produced in the same manner as in Example 1, except that the pressure-sensitive adhesive composition (4) was used instead of the pressure-sensitive adhesive composition (1).

[Example 5]

(Preparation of adhesive composition)

In place of the (meth)acrylic polymer (b1) 25 parts by mass (solid content 40% by mass ethyl acetate solution), 12.5 parts by mass of the (meth)acrylic polymer (b2) (solid content 40% by mass ethyl acetate solution) was used. Nate L (75% by weight solid content of trimethylolpropane/tolylenediisocyanate trimer adduct, ethyl acetate solution, manufactured by Nippon Polyurethane Industrial Co., Ltd.) in place of 4.0 parts by mass of Coronate HX (manufactured by Nippon Polyurethane Industrial Co., Ltd., iso Except having used 3.0 parts by mass of cyanurate-type hexamethylene diisocyanate crosslinking agent), it carried out similarly to Example 1, and prepared the adhesive composition (5).

(Production of adhesive sheet)

A pressure-sensitive adhesive sheet was produced in the same manner as in Example 1, except that the pressure-sensitive adhesive composition (5) was used instead of the pressure-sensitive adhesive composition (1).

[Example 6]

(Preparation of adhesive composition)

Instead of 25 parts by mass of the (meth)acrylic polymer (b1) (solid content 40% by mass ethyl acetate solution), 12.5 parts by mass of the (meth)acrylic polymer (b4) (solid content 40% by mass ethyl acetate solution) was used, and Nate L (75% by weight solid content of trimethylolpropane/tolylenediisocyanate trimer adduct, ethyl acetate solution, manufactured by Nippon Polyurethane Industrial Co., Ltd.) Except having used 3.0 parts by mass of cyanurate-type hexamethylene diisocyanate crosslinking agent), it carried out similarly to Example 1, and prepared the adhesive composition (6).

(Production of adhesive sheet)

A pressure-sensitive adhesive sheet was produced in the same manner as in Example 1 except that the pressure-sensitive adhesive composition (6) was used instead of the pressure-sensitive adhesive composition (1).

[Example 7]

(Preparation of adhesive composition)

Except for using the (meth)acrylic polymer (b3) 16.7 parts by mass (solid content 30% by mass ethyl acetate solution) instead of 25 parts by mass (solid content 40% by mass ethyl acetate solution), It carried out similarly to Example 1, and prepared the adhesive composition (8).

(Production of adhesive sheet)

A pressure-sensitive adhesive sheet was produced in the same manner as in Example 1, except that the pressure-sensitive adhesive composition (7) was used instead of the pressure-sensitive adhesive composition (1).

[Example 8]

(Preparation of adhesive composition)

Except for using the (meth)acrylic polymer (b5) 16.7 parts by mass (solid content 30% by mass ethyl acetate solution) instead of 25 parts by mass (solid content 40% by mass ethyl acetate solution), It carried out similarly to Example 1, and prepared the adhesive composition (8).

(Production of adhesive sheet)

A pressure-sensitive adhesive sheet was produced in the same manner as in Example 1, except that the pressure-sensitive adhesive composition (8) was used instead of the pressure-sensitive adhesive composition (1).

[Example 9]

(Preparation of adhesive composition)

In place of the (meth)acrylic polymer (b1) 25 parts by mass (solid content 40% by mass ethyl acetate solution), except for using 33.3 parts by mass of the (meth)acrylic polymer (b5) (solid content 30% by mass ethyl acetate solution), It carried out similarly to Example 1, and prepared the adhesive composition (9).

(Production of adhesive sheet)

A pressure-sensitive adhesive sheet was produced in the same manner as in Example 1, except that the pressure-sensitive adhesive composition (9) was used instead of the pressure-sensitive adhesive composition (1).

[Example 10]

(Preparation of adhesive composition)

In place of the (meth)acrylic polymer (b1) 25 parts by mass (solid content 40% by mass ethyl acetate solution), except for using 62.5 parts by mass of the (meth)acrylic polymer (b4) (solid content 40% by mass ethyl acetate solution), It carried out similarly to Example 1, and prepared the adhesive composition (10).

(Production of adhesive sheet)

A pressure-sensitive adhesive sheet was produced in the same manner as in Example 1, except that the pressure-sensitive adhesive composition (10) was used instead of the pressure-sensitive adhesive composition (1).

[Comparative Example 1]

(Preparation of adhesive composition)

To 500 parts by mass of a solution obtained by diluting the (meth)acrylic polymer (a) solution (35% by mass) to 20% by mass with ethyl acetate (100 parts by mass of the polymer), an alkali metal salt of bis (trifluoromethanesulfonyl) already 0.06 parts by mass of drytium (LiTFSI), 0.5 parts by mass of a polyether compound having a polyalkylene glycol chain (manufactured by Shin-Etsu Chemical Co., Ltd., KF6004), as a crosslinking agent, Coronate L (trimethylolpropane/tolylene diisocyanate A solid content of 75% by weight ethyl acetate solution of the nate trimer adduct, manufactured by Nippon Polyurethane Industrial Co., Ltd.) 3.3 parts by mass, and 3.0 parts by mass of dioctyl tin dilaurate (1% by weight ethyl acetate solution) as a crosslinking catalyst were added, and about at 25°C It mixed and stirred for 5 minutes, and the adhesive composition (11) was prepared.

(Production of adhesive sheet)

Except having used the said adhesive composition (11) instead of said adhesive composition (1), it carried out similarly to Example 1, and produced the adhesive sheet.

[Comparative Example 2]

(Preparation of adhesive composition)

To 500 parts by mass of a solution obtained by diluting the above adhesive polymer (1) solution (35% by mass) to 20% by mass with ethyl acetate (100 parts by mass of the polymer), 1-ethyl-3-methylimidazolium as a non-reactive ionic liquid 0.1 parts by mass of bis(fluorosulfonyl)imide (manufactured by Daiichi Pharmaceutical Co., Ltd., AS-110), 75 parts by mass of solid content of coronate L (trimethylolpropane/tolylenediisocyanate trimer adduct as a crosslinking agent) % Ethyl acetate solution, manufactured by Nippon Polyurethane Industrial Co., Ltd.) 3.3 parts by mass, and 3.0 parts by mass of dioctyl tin dilaurate (1 wt% ethyl acetate solution) as a crosslinking catalyst were added, and mixed and stirred at 25° C. for about 5 minutes to form a pressure-sensitive adhesive composition. (12) was prepared.

(Production of adhesive sheet)

A pressure-sensitive adhesive sheet was produced in the same manner as in Example 1, except that the pressure-sensitive adhesive composition 12 was used instead of the pressure-sensitive adhesive composition (1).

The abbreviations in Table 1 represent the following compounds. The negative number in Table 1 represents the solid content.

2EHA: 2-ethylhexyl acrylic acid

HEA: 2-hydroxyethyl acrylic acid

DMAEA-TFSI: 2-(acryloyloxy)ethyltrimethylammonium bis(trifluoromethanesulfonyl)imide (reactive ionic liquid)

DMAPAA-TFSI: (3-acrylamide propyl) trimethylammonium bis (trifluoromethanesulfonyl) imide (reactive ionic liquid)

PME1000: methoxy-terminated polyethylene glycol methacrylate (average number of moles added of ethylene oxide 23) (reactive monomer containing alkylene oxide group)

AS-110: 1-ethyl-3-methylimidazolium bis(fluorosulfonyl)imide (non-reactive ionic liquid)

LiTFSI: bis (trifluoromethanesulfonyl) imide lithium (alkali metal salt)

KF6004: Polyoxyalkylene-modified polydimethylsiloxane (polyether compound)

C/L (coronate L): trimethylolpropane/tolylenediisocyanate trimer addition (crosslinking agent)

C/HX (coronate HX): isocyanurate type hexamethylene diisocyanate (crosslinking agent)

(Measurement method and evaluation method)

<Measurement of molecular weight>

The weight average molecular weight (Mw) of the polymer (A) was measured using a GPC apparatus (manufactured by Tosoh Corporation, HLC-8220 GPC). Measurement conditions were as follows, and molecular weight was calculated|required by standard polystyrene conversion. Table 1 shows the measurement results.

Sample concentration: 0.2% by mass (tetrahydrofuran (THF) solution)

・Sample injection volume: 10µl

Eluent: THF

Flow rate: 0.6ml/min

·Measurement temperature: 40℃

·column:

Sample column: TSKguard column SuperHZ-H (1EA) + TSKgel SuperHZM-H (2EA)

Reference column: TSKgel SuperH-RC (1 pc.)

·Detector: Differential Refractometer (RI)

<Measurement of intrinsic viscosity>

The intrinsic viscosity (dL/g) of the polymer (B) was measured by a method in accordance with JIS-K7367-1. Measurement conditions are as follows. Table 1 shows the measurement results.

Sample concentration: Prepare 3 types of solutions in the range of 0.1 to 0.6 g/dL

Solvent: ethyl acetate

·Measurement temperature: 25℃

Equipment: Automatic capillary viscosity measuring device (manufactured by Shibayama Science Machinery Co., Ltd.)

Viscous tube: Ubelode type #1

<Measurement of gel fraction (solvent insoluble fraction)>

As for the solvent insoluble fraction (gel fraction), 0.1 g of the pressure-sensitive adhesive composition was sampled and accurately weighed (mass before immersion), and this was immersed in about 50 ml of ethyl acetate at room temperature (20 to 25°C) for 1 week, and then the solvent (acetic acid Ethyl) insolubles were taken out, and the solvent insolubles were dried at 130°C for 2 hours, then weighed (mass after immersion and drying), and calculated using the following formula for calculating the gel fraction (solvent insoluble fraction). Table 1 shows the measurement results.

Gel fraction (mass%) = [(mass after immersion and drying)/(mass before immersion)]×100

<Low-speed peeling test: 180° peeling (peeling) adhesion (adhesive force at the time of slow peeling)>

The adhesive sheet according to each Example and Comparative Example was cut into a size of 25 mm in width and 100 mm in length, and after peeling the release liner, the surface of a triacetylcellulose polarizing plate (manufactured by Nitto Denko, SEG1425DU, width: 70 mm, length: 100 mm) Then, after bonding with a hand roller, it laminated|laminated under the compression bonding conditions of 0.25 MPa and 0.3 m/min, and produced the evaluation sample (optical film with an adhesive sheet).

After the lamination, after allowing to stand for 30 minutes in an environment of 23°C x 50%RH, the opposite side of the triacetylcellulose polarizing plate was fixed to the acrylic plate with double-sided adhesive tape, and one end of the adhesive sheet was subjected to a tensile rate of 0.3 with a universal tensile tester. The adhesive force when peeled at m/min and peeling angle 180 degrees was measured. The measurement was performed in an environment of 23°C x 50% RH. Those having an adhesive force of 0.04 N/25 mm or more at the time of low-speed peeling were regarded as good, and those having an adhesive force of less than 0.04 N/25 mm were regarded as defective. Table 2 shows the measurement results.

<High-speed peeling test: 180° peeling (peeling) adhesive strength (adhesive force during high-speed peeling)>

The adhesive sheet according to each Example and Comparative Example was cut into a size of 25 mm in width and 100 mm in length, and after peeling the release liner, the surface of a triacetylcellulose polarizing plate (manufactured by Nitto Denko, SEG1425DU, width: 70 mm, length: 100 mm) Then, after bonding with a hand roller, it laminated|laminated under the compression bonding conditions of 0.25 MPa and 0.3 m/min, and produced the evaluation sample (optical film with an adhesive sheet).

After the lamination, after allowing to stand for 30 minutes in an environment of 23°C x 50%RH, the opposite side of the triacetylcellulose polarizing plate was fixed to the acrylic plate with double-sided adhesive tape, and one end of the adhesive sheet was subjected to a tensile speed of 30 m with a universal tensile tester The adhesive force when peeled at /min and peeling angle 180 degrees was measured. The measurement was performed in an environment of 23°C x 50% RH. Those having an adhesive force of 10 N/25 mm or less at the time of high-speed peeling were regarded as good, and those having an adhesive force exceeding 10 N/25 mm were regarded as defective. Table 2 shows the measurement results.

<Measurement of peeling large voltage>

The pressure-sensitive adhesive sheet 1 is cut into a size of 70 mm in width and 130 mm in length, and after the separator is peeled off, an acrylic plate 10 (manufactured by Mitsubishi Rayon, acrylic light, thickness: 1 mm, width: 70 mm) , Length: 100 mm), the polarizing plate 20 (manufactured by Nitto Denko, SEG1425DU, width: 70 mm, length: 100 mm) was pressed with a hand roller so that one end of the polarizing plate 20 was pushed out to the surface by 30 mm.

After leaving to stand for 1 day in an environment of 23°C x 50%RH, the sample is set to a predetermined position on the sample holder 30 as shown in FIG. 2. One end pushed out by 30 mm is fixed with an automatic winder, and peeled so that the peeling angle is 150° and the peeling speed is 10 m/min. The electric potential on the surface of the polarizing plate generated at this time was measured with a potential measuring device 40 (manufactured by Kasuga Electric Corporation, KSD-0103) fixed at a predetermined position, and was set as the value of the peeling electrification voltage. The measurement was carried out in an environment of 20°C×25%RH or 23°C×50%RH. On the other hand, as the peeling electrification voltage, those having an absolute value of 1.0 kV or less were regarded as good, and those having an absolute value exceeding 1.0 kV were regarded as defective. Table 2 shows the measurement results.

<Transparency Test: Initial Haze>

After cutting the pressure-sensitive adhesive sheet according to each Example and Comparative Example to a size of 50 mm in width and 50 mm in length, the release liner was peeled off, and the haze was measured with a haze meter (manufactured by Murakami Color Technology Research Institute Co., Ltd.). A haze of less than 10% was regarded as good, and a haze of 10% or more was regarded as defective. Table 2 shows the measurement results.

As shown in Table 2, in the case of using the adhesive sheet (antistatic adhesive sheet) produced according to the present invention (Examples 1 to 10), the peeling voltage was within ±1.0 kV, excellent antistatic property, and low speed The adhesive force at the time of peeling and the adhesive force at the time of high-speed peeling were also included in the desired range, and it was confirmed that the re-peelability and adhesiveness were excellent, and the transparency was also satisfied.

In contrast, in Comparative Example 1, lithium salts and polyether compounds were used as additives (antistatic agents), but since polymer (B) was not used, antistatic properties were obtained, but adhesive strength at low speed peeling was insufficient. Became. In addition, in Comparative Example 2, since a small amount of non-reactive ionic liquid was used as an additive (antistatic agent) and no polymer (B) was used, the adhesive strength at the time of low-speed peeling was sufficient. The prevention property became insufficient.

1: electric potential meter
2: adhesive sheet
3: polarizer
4: acrylic plate
5: fixture
10: adhesive sheet (antistatic adhesive sheet)
11: separator
12: adhesive layer
13: base film

Claims (15)

A polymer (A) having a glass transition temperature of less than 0° C., and
It contains a reactive ionic liquid as a monomer unit, and contains a polymer (B) having an intrinsic viscosity (dL/g) of 0.01 or more and less than 0.5,
The polymer (B) contains a monomer having a polyoxyalkylene skeleton as a monomer unit,
The pressure-sensitive adhesive composition, wherein the reactive ionic liquid is a reactive ionic liquid represented by the following Chemical Formulas 1 and/or 2.
[Formula 1]

[Formula 2]

[In Formulas 1 and 2, R ¹ is a hydrogen atom or a methyl group, X ⁺ is a cation ^{moiety, and Y-} is an anion. Z represents a C1-C3 alkylene group.] The method of claim 1,
A pressure-sensitive adhesive composition comprising 0.05 to 30 parts by mass of the polymer (B) with respect to 100 parts by mass of the polymer (A). The method of claim 1,
The pressure-sensitive adhesive composition, wherein the polymer (B) is a (meth)acrylic polymer. delete delete The method of claim 1,
The pressure-sensitive adhesive composition, characterized in that the cation portion is a quaternary ammonium group. The method of claim 1,
The pressure-sensitive adhesive composition, characterized in that the anion is a fluorine-containing anion. The method of claim 1,
The pressure-sensitive adhesive composition, wherein the monomer having a polyoxyalkylene skeleton is an alkylene oxide group-containing reactive monomer having an average added mole number of 3 to 100 oxyalkylene units. A pressure-sensitive adhesive layer formed of the pressure-sensitive adhesive composition according to any one of claims 1 to 3 and 6 to 8. The method of claim 9,
The pressure-sensitive adhesive layer, wherein the gel fraction is 85.00 to 99.95% by mass. A pressure-sensitive adhesive sheet formed by forming the pressure-sensitive adhesive layer according to claim 9 on at least one side of a base film. The method of claim 11,
The adhesive sheet, characterized in that the base film is a plastic film. The method of claim 11,
A pressure-sensitive adhesive sheet for use in surface protection applications. The method of claim 11,
A pressure-sensitive adhesive sheet used in an electronic component manufacturing and shipping process. An optical film with a pressure-sensitive adhesive sheet, wherein the pressure-sensitive adhesive sheet according to claim 13 is attached to an optical film.

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